How to get from Boston, MA to Chicago

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What is the best way to travel from Boston, MA to Chicago?

Looking for a trip? Check and compare all the available Flights and Buses to Chicago from Boston, MA. Look at different modes of transportation, search for the cheapest tickets, fastest rides and most popular stations, and see all 2 available companies to find your perfect trip!
Flight is the cheapest and fastest way on this route
Transport type
Travel time
Cheapest price
Average price
Daily departures
Bus
22h 30m
£71
£90
32
Flight
2h 40m
£58
£148
87

What is the cheapest way to reach Chicago from Boston, MA?

You can reach Chicago with just £58 by taking a Flight from United Airlines, but there are many more cheap offers: we have selected the best ones for you for the next few days here.

Monday
from £83
Tuesday
from £82
Wednesday
from £65
Thursday
from £58
Friday
from £59
Saturday
from £58
Sunday
from £73

    Cheapest Buses Monday

  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £83
  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    South Station
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £84
  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £84
  • FlixBus
    35h 20m
    0
    22:00
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £84
  • FlixBus
    33h 45m
    0
    20:55
    Boston, MA
    Allston
    05:40
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £84
  • Cheapest Flights Monday

  • United Airlines
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £119
  • Spirit Airlines
    29h 8m
    0
    20:16
    Boston Logan Airport
    Boston Logan Airport
    00:24
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £128
  • Frontier Airlines
    7h 49m
    0
    12:42
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £143
  • Frontier Airlines
    21h 58m
    0
    12:42
    Boston Logan Airport
    Boston Logan Airport
    09:40
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £145
  • Sun Country Airlines
    7h 43m
    0
    11:17
    Boston Logan Airport
    Boston Logan Airport
    18:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Sun Country Airlines
    Economy
    from £151
  • Spirit Airlines
    26h 31m
    0
    18:00
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Spirit Airlines
    Economy
    from £152

    Cheapest Flights Tuesday

  • Spirit Airlines
    14h 20m
    0
    20:16
    Boston Logan Airport
    Boston Logan Airport
    09:36
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £82
  • Frontier Airlines
    7h 51m
    0
    12:40
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £101
  • Frontier Airlines
    12h 0m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    17:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £105
  • Frontier Airlines
    17h 14m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    22:14
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £133
  • United Airlines
    5h 13m
    0
    19:30
    Boston Logan Airport
    Boston Logan Airport
    23:43
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £144
  • JetBlue Airways
    12h 26m
    0
    20:15
    Boston Logan Airport
    Boston Logan Airport
    07:41
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £170
  • Cheapest Buses Tuesday

  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £117
  • Greyhound US
    31h 50m
    0
    16:45
    Boston, MA
    Atlantic and Beach St
    23:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £117
  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    South Station
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £120
  • FlixBus
    35h 20m
    0
    22:00
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £120
  • FlixBus
    33h 45m
    0
    20:55
    Boston, MA
    Allston
    05:40
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £122

    Cheapest Flights Wednesday

  • JetBlue Airways
    3h 4m
    0
    19:35
    Boston Logan Airport
    Boston Logan Airport
    21:39
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £65
  • United Airlines
    2h 59m
    0
    07:15
    Boston Logan Airport
    Boston Logan Airport
    09:14
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £66
  • Frontier Airlines
    7h 36m
    0
    12:55
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £67
  • Frontier Airlines
    12h 0m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    17:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £72
  • Spirit Airlines
    14h 20m
    0
    20:16
    Boston Logan Airport
    Boston Logan Airport
    09:36
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £82
  • Frontier Airlines
    17h 14m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    22:14
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £109
  • Cheapest Buses Wednesday

  • FlixBus
    28h 40m
    0
    02:30
    Boston, MA
    Atlantic and Beach St
    06:10
    Chicago
    Downtown Coach Station
    0
    FlixBus
    Economy
    £82
  • Greyhound US
    29h 10m
    0
    01:30
    Boston, MA
    Atlantic and Beach St
    05:40
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £83
  • Greyhound US
    29h 50m
    0
    08:55
    Boston, MA
    Atlantic and Beach St
    13:45
    Chicago
    Canal & Van Buren
    0
    Greyhound US
    Economy
    £83
  • Greyhound US
    22h 30m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    10:00
    Chicago
    Downtown Coach Station
    0
    Greyhound US
    Economy
    £83
  • FlixBus
    29h 40m
    0
    01:30
    Boston, MA
    Allston
    06:10
    Chicago
    Downtown Coach Station
    0
    FlixBus
    Economy
    £83

    Cheapest Flights Thursday

  • United Airlines
    2h 59m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    07:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £58
  • JetBlue Airways
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £65
  • Frontier Airlines
    7h 2m
    0
    12:31
    Boston Logan Airport
    Boston Logan Airport
    18:33
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £83
  • Spirit Airlines
    13h 39m
    0
    11:20
    Boston Logan Airport
    Boston Logan Airport
    23:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £91
  • Frontier Airlines
    14h 31m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £115
  • Spirit Airlines
    27h 27m
    0
    15:27
    Boston Logan Airport
    Boston Logan Airport
    17:54
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Spirit Airlines
    Economy
    from £123
  • Cheapest Buses Thursday

  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £71
  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £73
  • Greyhound US
    31h 50m
    0
    16:45
    Boston, MA
    Atlantic and Beach St
    23:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £73
  • FlixBus
    35h 20m
    0
    22:00
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £87
  • FlixBus
    35h 0m
    0
    22:00
    Boston, MA
    South Station
    08:00
    Chicago
    Union Station
    0
    FlixBus
    Economy
    £87

    Cheapest Flights Friday

  • American Airlines
    3h 17m
    0
    17:35
    Boston Logan Airport
    Boston Logan Airport
    19:52
    Chicago Midway Airport
    Chicago Midway Airport
    0
    American Airlines
    Economy
    from £59
  • American Airlines
    2h 50m
    0
    18:55
    Boston Logan Airport
    Boston Logan Airport
    20:45
    Chicago Midway Airport
    Chicago Midway Airport
    0
    American Airlines
    Economy
    from £59
  • United Airlines
    2h 59m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    07:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £59
  • United Airlines
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £59
  • Spirit Airlines
    18h 59m
    0
    05:55
    Boston Logan Airport
    Boston Logan Airport
    23:54
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £91
  • Spirit Airlines
    26h 1m
    0
    20:16
    Boston Logan Airport
    Boston Logan Airport
    21:17
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £91
  • Cheapest Buses Friday

  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £84
  • Greyhound US
    31h 5m
    0
    02:15
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £85
  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £85
  • FlixBus
    35h 20m
    0
    22:00
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £87
  • FlixBus
    33h 45m
    0
    20:55
    Boston, MA
    Allston
    05:40
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £88

    Cheapest Flights Saturday

  • United Airlines
    3h 0m
    0
    16:28
    Boston Logan Airport
    Boston Logan Airport
    18:28
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £58
  • JetBlue Airways
    3h 4m
    0
    19:35
    Boston Logan Airport
    Boston Logan Airport
    21:39
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £58
  • Spirit Airlines
    13h 39m
    0
    11:20
    Boston Logan Airport
    Boston Logan Airport
    23:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £84
  • Frontier Airlines
    17h 14m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    22:14
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £101
  • Frontier Airlines
    13h 37m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    18:37
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £104
  • Frontier Airlines
    27h 9m
    0
    11:06
    Boston Logan Airport
    Boston Logan Airport
    13:15
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £105
  • Cheapest Buses Saturday

  • Greyhound US
    23h 20m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    Downtown Coach Station
    0
    Greyhound US
    Economy
    £88
  • FlixBus
    30h 30m
    0
    02:30
    Boston, MA
    Atlantic and Beach St
    08:00
    Chicago
    Canal & Van Buren
    0
    FlixBus
    Economy
    £88
  • Greyhound US
    22h 30m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    10:00
    Chicago
    Downtown Coach Station
    0
    Greyhound US
    Economy
    £89
  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £90
  • FlixBus
    30h 50m
    0
    02:30
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £90

    Cheapest Flights Sunday

  • JetBlue Airways
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago Midway Airport
    Chicago Midway Airport
    0
    JetBlue Airways
    Economy
    from £73
  • JetBlue Airways
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £79
  • United Airlines
    2h 59m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    07:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £80
  • JetBlue Airways
    2h 40m
    0
    10:35
    Boston Logan Airport
    Boston Logan Airport
    12:15
    Chicago Midway Airport
    Chicago Midway Airport
    0
    JetBlue Airways
    Economy
    from £81
  • Frontier Airlines
    11h 30m
    0
    12:31
    Boston Logan Airport
    Boston Logan Airport
    23:01
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £85
  • Spirit Airlines
    20h 5m
    0
    18:00
    Boston Logan Airport
    Boston Logan Airport
    13:05
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £156
  • Cheapest Buses Sunday

  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £89
  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    South Station
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £90
  • Greyhound US
    29h 10m
    0
    01:30
    Boston, MA
    Atlantic and Beach St
    05:40
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £90
  • FlixBus
    30h 50m
    0
    02:30
    Boston, MA
    South Station
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £90
  • FlixBus
    30h 50m
    0
    02:30
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £90

What are the fastest trips from Boston, MA to Chicago?

You can get to Chicago from Boston, MA in just 2h 40m with a Flight from JetBlue Airways. But this is just one option, click on any of the offers below to compare it with the other available modes of transportations.

Monday
from 3h 0m
Tuesday
from 5h 13m
Wednesday
from 2h 59m
Thursday
from 2h 59m
Friday
from 2h 50m
Saturday
from 3h 0m
Sunday
from 2h 40m

    Fastest Flights Monday

  • United Airlines
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £119
  • JetBlue Airways
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £170
  • Sun Country Airlines
    7h 43m
    0
    11:17
    Boston Logan Airport
    Boston Logan Airport
    18:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Sun Country Airlines
    Economy
    from £151
  • Frontier Airlines
    7h 49m
    0
    12:42
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £143
  • Frontier Airlines
    21h 58m
    0
    12:42
    Boston Logan Airport
    Boston Logan Airport
    09:40
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £145
  • Delta Air Lines
    23h 21m
    0
    11:54
    Boston Logan Airport
    Boston Logan Airport
    10:15
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Delta Air Lines
    Economy
    from £313
  • Fastest Buses Monday

  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £83
  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    South Station
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £84
  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £84
  • FlixBus
    33h 45m
    0
    20:55
    Boston, MA
    Allston
    05:40
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £84
  • FlixBus
    35h 20m
    0
    22:00
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £84

    Fastest Flights Tuesday

  • United Airlines
    5h 13m
    0
    19:30
    Boston Logan Airport
    Boston Logan Airport
    23:43
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £144
  • Frontier Airlines
    7h 51m
    0
    12:40
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £101
  • Frontier Airlines
    12h 0m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    17:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £105
  • JetBlue Airways
    12h 26m
    0
    20:15
    Boston Logan Airport
    Boston Logan Airport
    07:41
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £170
  • Spirit Airlines
    14h 20m
    0
    20:16
    Boston Logan Airport
    Boston Logan Airport
    09:36
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £82
  • Frontier Airlines
    17h 14m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    22:14
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £133
  • Fastest Buses Tuesday

  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £117
  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    South Station
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £120
  • Greyhound US
    31h 50m
    0
    16:45
    Boston, MA
    Atlantic and Beach St
    23:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £117
  • FlixBus
    33h 45m
    0
    20:55
    Boston, MA
    Allston
    05:40
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £122
  • FlixBus
    35h 20m
    0
    22:00
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £120

    Fastest Flights Wednesday

  • United Airlines
    2h 59m
    0
    07:15
    Boston Logan Airport
    Boston Logan Airport
    09:14
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £66
  • JetBlue Airways
    3h 4m
    0
    19:35
    Boston Logan Airport
    Boston Logan Airport
    21:39
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £65
  • Frontier Airlines
    7h 36m
    0
    12:55
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £67
  • Frontier Airlines
    12h 0m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    17:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £72
  • Spirit Airlines
    14h 20m
    0
    20:16
    Boston Logan Airport
    Boston Logan Airport
    09:36
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £82
  • Frontier Airlines
    14h 31m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £113
  • Fastest Buses Wednesday

  • Greyhound US
    22h 30m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    10:00
    Chicago
    Downtown Coach Station
    0
    Greyhound US
    Economy
    £83
  • FlixBus
    28h 40m
    0
    02:30
    Boston, MA
    Atlantic and Beach St
    06:10
    Chicago
    Downtown Coach Station
    0
    FlixBus
    Economy
    £82
  • Greyhound US
    29h 10m
    0
    01:30
    Boston, MA
    Atlantic and Beach St
    05:40
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £83
  • FlixBus
    29h 40m
    0
    01:30
    Boston, MA
    Allston
    06:10
    Chicago
    Downtown Coach Station
    0
    FlixBus
    Economy
    £83
  • Greyhound US
    29h 50m
    0
    08:55
    Boston, MA
    Atlantic and Beach St
    13:45
    Chicago
    Canal & Van Buren
    0
    Greyhound US
    Economy
    £83

    Fastest Flights Thursday

  • United Airlines
    2h 59m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    07:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £58
  • JetBlue Airways
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £65
  • Frontier Airlines
    7h 2m
    0
    12:31
    Boston Logan Airport
    Boston Logan Airport
    18:33
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £83
  • Sun Country Airlines
    8h 1m
    0
    11:17
    Boston Logan Airport
    Boston Logan Airport
    18:18
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Sun Country Airlines
    Economy
    from £179
  • Spirit Airlines
    13h 39m
    0
    11:20
    Boston Logan Airport
    Boston Logan Airport
    23:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £91
  • Frontier Airlines
    14h 31m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    19:31
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £115
  • Fastest Buses Thursday

  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £73
  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £71
  • Greyhound US
    31h 50m
    0
    16:45
    Boston, MA
    Atlantic and Beach St
    23:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £73
  • FlixBus
    35h 0m
    0
    22:00
    Boston, MA
    South Station
    08:00
    Chicago
    Union Station
    0
    FlixBus
    Economy
    £87
  • FlixBus
    35h 20m
    0
    22:00
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £87

    Fastest Flights Friday

  • American Airlines
    2h 50m
    0
    18:55
    Boston Logan Airport
    Boston Logan Airport
    20:45
    Chicago Midway Airport
    Chicago Midway Airport
    0
    American Airlines
    Economy
    from £59
  • United Airlines
    2h 59m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    07:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £59
  • United Airlines
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £59
  • American Airlines
    3h 17m
    0
    17:35
    Boston Logan Airport
    Boston Logan Airport
    19:52
    Chicago Midway Airport
    Chicago Midway Airport
    0
    American Airlines
    Economy
    from £59
  • Frontier Airlines
    17h 26m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    22:26
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £116
  • Frontier Airlines
    17h 39m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    22:39
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Frontier Airlines
    Economy
    from £116
  • Fastest Buses Friday

  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £85
  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £84
  • Greyhound US
    31h 5m
    0
    02:15
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £85
  • FlixBus
    33h 45m
    0
    20:55
    Boston, MA
    Allston
    05:40
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £88
  • FlixBus
    35h 20m
    0
    22:00
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £87

    Fastest Flights Saturday

  • United Airlines
    3h 0m
    0
    16:28
    Boston Logan Airport
    Boston Logan Airport
    18:28
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £58
  • JetBlue Airways
    3h 4m
    0
    19:35
    Boston Logan Airport
    Boston Logan Airport
    21:39
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £58
  • Frontier Airlines
    13h 37m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    18:37
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £104
  • Spirit Airlines
    13h 39m
    0
    11:20
    Boston Logan Airport
    Boston Logan Airport
    23:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Spirit Airlines
    Economy
    from £84
  • Alaska Airlines
    13h 52m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    19:52
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Alaska Airlines
    Economy
    from £255
  • Frontier Airlines
    17h 14m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    22:14
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £101
  • Fastest Buses Saturday

  • Greyhound US
    22h 30m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    10:00
    Chicago
    Downtown Coach Station
    0
    Greyhound US
    Economy
    £89
  • Greyhound US
    23h 20m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    Downtown Coach Station
    0
    Greyhound US
    Economy
    £88
  • Greyhound US
    25h 55m
    0
    12:30
    Boston, MA
    Atlantic and Beach St
    13:25
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £90
  • FlixBus
    30h 30m
    0
    02:30
    Boston, MA
    Atlantic and Beach St
    08:00
    Chicago
    Canal & Van Buren
    0
    FlixBus
    Economy
    £88
  • FlixBus
    30h 50m
    0
    02:30
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £90

    Fastest Flights Sunday

  • JetBlue Airways
    2h 40m
    0
    10:35
    Boston Logan Airport
    Boston Logan Airport
    12:15
    Chicago Midway Airport
    Chicago Midway Airport
    0
    JetBlue Airways
    Economy
    from £81
  • United Airlines
    2h 59m
    0
    06:00
    Boston Logan Airport
    Boston Logan Airport
    07:59
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    United Airlines
    Economy
    from £80
  • JetBlue Airways
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago Midway Airport
    Chicago Midway Airport
    0
    JetBlue Airways
    Economy
    from £73
  • JetBlue Airways
    3h 0m
    0
    07:00
    Boston Logan Airport
    Boston Logan Airport
    09:00
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    JetBlue Airways
    Economy
    from £79
  • Sun Country Airlines
    9h 48m
    0
    09:00
    Boston Logan Airport
    Boston Logan Airport
    17:48
    Chicago O'Hare Airport
    Chicago O'Hare Airport - Bus/Shuttle Center
    0
    Sun Country Airlines
    Economy
    from £207
  • Frontier Airlines
    10h 51m
    0
    12:28
    Boston Logan Airport
    Boston Logan Airport
    22:19
    Chicago Midway Airport
    Chicago Midway Airport
    0
    Frontier Airlines
    Economy
    from £182
  • Fastest Buses Sunday

  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    Atlantic and Beach St
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £89
  • Greyhound US
    28h 30m
    0
    15:05
    Boston, MA
    South Station
    18:35
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £90
  • Greyhound US
    29h 10m
    0
    01:30
    Boston, MA
    Atlantic and Beach St
    05:40
    Chicago
    95th Red Line Station
    0
    Greyhound US
    Economy
    £90
  • FlixBus
    30h 50m
    0
    02:30
    Boston, MA
    South Station
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £90
  • FlixBus
    30h 50m
    0
    02:30
    Boston, MA
    Atlantic and Beach St
    08:20
    Chicago
    95th Red Line Station
    0
    FlixBus
    Economy
    £90
Here you will find all operators and timetables for a Bus from Boston, MA to Chicago

What are the most popular stations in Boston, MA and Chicago?

In Boston, MA, you will usually depart from Atlantic and Beach St, South Station or Logan Office Center Coach Stop, while in Chicago you will be arriving at Downtown Coach Station, 95th Red Line Station or California & 35th Street Coach Stop, but there are many more stops to explore in both locations.

How do I decide? Some tips and tricks from our experience

Are you having trouble deciding on how to get to Chicago from Boston, MA? With 15 connections between 2 Flight and Bus operators, it can be difficult to find the one ride that will make you happy. But we have some tips that can help you make the best informed decision. First of all, the best trip is always the one that meets all your needs, so make a list of all the things that you want from this journey and look for something that will satisfy all of them. Here we will go through some of the factors mostly commonly taken into consideration.

Look for the lowest price

Ticket price is usually the main concern: even if you can afford to pay more, why do it if there are cheaper options? Saving on the trip means that you can spend more on the vacation itself! Between Boston, MA and Chicago, you can pay as low as £58 with a Flight from United Airlines.

Travel duration

Time is also an important factor. An earlier departure may allow you to see a beautiful sunset or relax before an important event. And remember, time is money, so paying more for a shorter trip may be well worth it. For longer distances, flights are without doubt the best options, but be mindful of airport times and possible delays: a high-speed train may end up cheaper and faster! Here the quicker option is definitely the Flight from JetBlue Airways: you will get to Chicago in just 2h 40m.

Comfort makes all the difference

You should always take into account what your personal travelling preferences are. Is one hand luggage enough, or are you trasporting more? Would you like to have a snack during the journey? Can you relax in a busy compartment, or do you need space for yourself? Even among the same mode of transportation, different companies will offer you varying levels of comfort and amenities. The main operators connecting Boston, MA and Chicago are Frontier Airlines, Greyhound US and Spirit Airlines, but be sure to check what they have to offer!

Save money with deals, and always compare

One last tip? Even if you live in Boston, MA and Chicago is your only destination, it may be wise to check the offers from and to nearby cities or, if you are flyng, nearby airports. Check the trips from Boston Logan Airport or to Cicero, IL, and look at flights from Boston Logan Airport, and landing at Chicago Midway Airport. Comparing different routes may allow you to find deals or promotions you were not aware of. Consider also signing up to CheckMyBus to see even more exclusive promotions!

Which companies offer a trip from Boston, MA to Chicago?

The most popular companies between Boston, MA and Chicago, are Frontier Airlines, Greyhound US and Spirit Airlines. Be sure to check their seat class offers and the amenities that they provide.

Bus companies: Greyhound US and FlixBus

Airlines: Frontier Airlines, Spirit Airlines, JetBlue Airways and 8 more.

All you need to know when you travel from Boston, MA to Chicago

Check all information on comfort and services on all modes of transports from Boston, MA to Chicago. See which seat classes are available, and what amenities are other advantages offered by the operators on your journey.

FAQs about the trip from Boston, MA to Chicago

How can I reach Chicago from Boston, MA?

Every day, there are on average 15 connections between Flight and Bus, with which you can get to Chicago from Boston, MA.

How far is Chicago from Boston, MA?

The distance between Boston, MA and Chicago is 1,366.8 km.

What is the most ecofriendly mode of transport between Boston, MA and Chicago?

Trains and buses are by far the greenest options, with trains surpassing buses on longer routes. Planes will always be the worst polluters, especially in shorter flights, were the emissions from the takeoff and landing are less offset by the distance. On this particular route, a bus will emit, per person, a total of 37 kgs of CO2, a train 48 kgs, a car 232 kgs, and a flight 336 kgs.

What is the cheapest mode of transport from Boston, MA to Chicago?

You can get to Chicago with just £58 by taking a Flight from United Airlines.

What is the fastest way to get from Boston, MA to Chicago?

While a plane is travelling fastest boarding and transfer to airport consumes a lot of time. Usually, high speed trains are better than flights if pure train travel time is below 4 hours. For this particular route, you can get to Chicago in just 2h 40m with a Flight from JetBlue Airways.

More routes to Boston, MA and to Chicago

Looking for more options? Here you can see the most popular routes to Boston, MA and to Chicago. Simply click on a connection, and you’ll find all the details about the route!

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