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Cheap flights from Boston to Chicago

49 nonstop flights a week, 5 of them today. Operated by 5 airlines, about 3h 3m in the air, 849 mi (1,366 km). Tickets from $119, nonstop from $114.

Flights from Boston to Chicago

Pick a departure date to see flights and seller prices

We search agencies and airlines for your day: nonstop and connecting flights, baggage, departure and arrival times.

Prices by day: Boston to Chicago

Lowest one-way price in dollars from recent searches, cheap days in green. Press a day to see flights and exact prices.

Filters

Best fares from Boston to Chicago

Lowest one-way prices found by recent searches for the next 120 days; press a card to search that date

Cheapest one-way $114 11 November 2026, nonstop Cheapest nonstop $114 11 November 2026, American Airlines Cheapest in the next 7 days $114 Today Cheapest weekend departure $119 Sat, 21 November 2026 Cheapest month November 2026 tickets from $114

Boston to Chicago at a glance

flight time, from 2h 40m to 3h 22m
3h 3m
straight-line distance
849 mi (1,366 km)
flights a week
49
flights today
5
first and last departure
05:39 - 07:45
lowest price, nonstop, 21 November
$119
lowest nonstop price
$114
airlines
5

Boston to Chicago ticket prices by month

Lowest one-way fare found by recent searches

Cheapest month: November 2026, tickets from $114. Prices come from searches over the last few days; check the search for your exact date.

The most expensive month is March 2027: from $183. The average across months is $141.

Boston to Chicago flight schedule

49 flights a week, 5 today, 48 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
AA 421
American Airlines
05:39 Logan International, terminal B
08:00 , terminal 3
3h 21m
Mon, Thu, Fri, Sun
Boeing 737-800
AA 2146
American Airlines
05:43 Logan International, terminal B
08:00 , terminal 3
3h 17m
Daily
Boeing 737-800
UA 1414
United Airlines
06:00 Logan International, terminal B
08:00 , terminal 1
3h
Daily
Boeing 737
WN 845
Southwest Airlines
06:25 Logan International, terminal B
08:15 Chicago Midway International
2h 50m
Sat
AA 340
American Airlines
06:38 Logan International, terminal B
09:00 , terminal 3
3h 22m
Sat
Airbus A319
WN 2185
Southwest Airlines
07:05 Logan International, terminal B
08:50 Chicago Midway International
2h 45m
Mon, Thu, Fri, Sun
WN 4995
Southwest Airlines
07:10 Logan International, terminal B
08:55 Chicago Midway International
2h 45m
Mon, Tue, Wed, Thu
Boeing 737
AA 947
American Airlines
07:13 Logan International, terminal B
09:35 , terminal 3
3h 22m
Mon, Thu, Fri, Sun
Airbus A321
AA 947
American Airlines
07:14 Logan International, terminal B
09:30 , terminal 3
3h 16m
Daily
Airbus A321
DL 2570
Delta
07:30 Logan International, terminal A
09:35 , terminal 5
3h 5m
Mon, Tue, Wed, Thu, Fri, Sun
Boeing 737-800
UA 1834
United Airlines
07:31 Logan International, terminal B
09:34 , terminal 1
3h 3m
Daily
Airbus A320
AA 947
American Airlines
07:37 Logan International, terminal B
09:59 , terminal 3
3h 22m
Sat
Airbus A321
DL 2570
Delta
07:45 Logan International, terminal A
09:55 , terminal 5
3h 10m
Sat
Airbus A220-300

Seasonal and one-off flights

Not operating in the next two weeks. The first of them is on 24 November.

FlightDepartsArrivesDurationDaysAircraft
WN 4999
Southwest Airlines
07:00 Logan International, terminal B
08:45 Chicago Midway International
2h 45m
Seasonal
Boeing 737
AA 340
American Airlines
06:48 Logan International, terminal B
09:10 , terminal 3
3h 22m
Seasonal
Airbus A321
WN 4999
Southwest Airlines
07:15 Logan International, terminal B
09:05 Chicago Midway International
2h 50m
Seasonal
Boeing 737
WN 2972
Southwest Airlines
06:45 Logan International, terminal B
08:30 Chicago Midway International
2h 45m
Seasonal
AA 1379
American Airlines
05:53 Logan International, terminal B
08:04 , terminal 3
3h 11m
Seasonal
Boeing 737-800
AA 2146
American Airlines
07:15 Logan International, terminal B
09:30 , terminal 3
3h 15m
Seasonal
Airbus A321
WN 4995
Southwest Airlines
07:15 Logan International, terminal B
09:00 Chicago Midway International
2h 45m
Seasonal
Boeing 737
DL 2570
Delta
07:40 Logan International, terminal A
09:51 , terminal 5
3h 11m
Seasonal
Airbus A220-300
UA 1414
United Airlines
05:45 Logan International, terminal B
07:50 , terminal 1
3h 5m
Seasonal
Boeing 737
AA 947
American Airlines
05:51 Logan International, terminal B
08:04 , terminal 3
3h 13m
Seasonal
Airbus A320
AA 2544
American Airlines
07:20 Logan International, terminal B
09:35 , terminal 3
3h 15m
Seasonal
Airbus A321
AA 3355
American Airlines
07:38 Logan International, terminal B
10:00 , terminal 3
3h 22m
Seasonal
Embraer 170
AA 947
American Airlines
06:12 Logan International, terminal B
08:25 , terminal 3
3h 13m
Seasonal
Airbus A320
AA 4487
American Airlines
07:40 Logan International, terminal B
10:00 , terminal 3
3h 20m
Seasonal
Embraer EMB 175
DL 5594
Delta
07:30 Logan International, terminal A
09:33 , terminal 5
3h 3m
Seasonal
Embraer EMB 175
AA 3165
American Airlines
06:05 Logan International, terminal B
08:20 , terminal 3
3h 15m
Seasonal
Boeing 737-800
AA 1328
American Airlines
07:10 Logan International, terminal B
09:30 , terminal 3
3h 20m
Seasonal
Airbus A321
WN 4127
Southwest Airlines
07:10 Logan International, terminal B
09:10 Chicago Midway International
3h
Seasonal
Boeing 737
WN 4127
Southwest Airlines
07:15 Logan International, terminal B
09:15 Chicago Midway International
3h
Seasonal
Boeing 737
AA 3165
American Airlines
06:15 Logan International, terminal B
08:30 , terminal 3
3h 15m
Seasonal
Boeing 737-800
AA 1328
American Airlines
07:05 Logan International, terminal B
09:25 , terminal 3
3h 20m
Seasonal
Airbus A321
AA 3189
American Airlines
05:49 Logan International, terminal B
07:58 , terminal 3
3h 9m
Seasonal
Boeing 737-800
WN 4127
Southwest Airlines
06:35 Logan International, terminal B
08:30 Chicago Midway International
2h 55m
Seasonal
Boeing 737
AA 1328
American Airlines
07:16 Logan International, terminal B
09:30 , terminal 3
3h 14m
Seasonal
Airbus A321
AA 3324
American Airlines
05:49 Logan International, terminal B
07:58 , terminal 3
3h 9m
Seasonal
Boeing 737-800
UA 2631
United Airlines
07:45 Logan International, terminal B
09:42 , terminal 1
2h 57m
Seasonal
Boeing 737-800
DL 3161
Delta
07:30 Logan International, terminal A
09:33 , terminal 5
3h 3m
Seasonal
Airbus A220-300
WN 4695
Southwest Airlines
07:30 Logan International, terminal B
09:15 Chicago Midway International
2h 45m
Seasonal
Boeing 737-800
WN 4679
Southwest Airlines
07:05 Logan International, terminal B
08:55 Chicago Midway International
2h 50m
Seasonal
Boeing 737
WN 4695
Southwest Airlines
07:00 Logan International, terminal B
08:50 Chicago Midway International
2h 50m
Seasonal
Boeing 737
UA 2631
United Airlines
07:10 Logan International, terminal B
09:08 , terminal 1
2h 58m
Seasonal
Airbus A320
AA 1509
American Airlines
06:30 Logan International, terminal B
08:44 , terminal 3
3h 14m
Seasonal
Boeing 737-800
WN 4654
Southwest Airlines
07:30 Logan International, terminal B
09:15 Chicago Midway International
2h 45m
Seasonal
Boeing 737-800
WN 4654
Southwest Airlines
06:40 Logan International, terminal B
08:25 Chicago Midway International
2h 45m
Seasonal
Boeing 737
WN 4654
Southwest Airlines
07:20 Logan International, terminal B
09:05 Chicago Midway International
2h 45m
Seasonal
Boeing 737-800
DL 3161
Delta
07:00 Logan International, terminal A
09:03 , terminal 5
3h 3m
Seasonal
Boeing 737-800
B6 311
jetBlue
06:00 Logan International, terminal C
08:00 , terminal 2
3h
Seasonal
Airbus A220-300
AA 2939
American Airlines
05:05 Logan International, terminal B
07:02 , terminal 3
2h 57m
Seasonal
Boeing 737-800
AA 1509
American Airlines
07:00 Logan International, terminal B
09:04 , terminal 3
3h 4m
Seasonal
Boeing 737-800
AA 1509
American Airlines
05:00 Logan International, terminal B
06:58 , terminal 3
2h 58m
Seasonal
Boeing 737-800
AA 1785
American Airlines
07:00 Logan International, terminal B
09:03 , terminal 3
3h 3m
Seasonal
Boeing 737-800
WN 632
Southwest Airlines
06:30 Logan International, terminal B
08:10 Chicago Midway International
2h 40m
Seasonal
WN 1286
Southwest Airlines
07:40 Logan International, terminal B
09:20 Chicago Midway International
2h 40m
Seasonal
Boeing 737
WN 5325
Southwest Airlines
06:30 Logan International, terminal B
08:10 Chicago Midway International
2h 40m
Seasonal
Boeing 737
WN 632
Southwest Airlines
07:15 Logan International, terminal B
08:55 Chicago Midway International
2h 40m
Seasonal
AA 1509
American Airlines
05:10 Logan International, terminal B
07:04 , terminal 3
2h 54m
Seasonal
Boeing 737-800
AA 1509
American Airlines
06:24 Logan International, terminal B
08:30 , terminal 3
3h 6m
Seasonal
Boeing 737-800
AA 1785
American Airlines
07:10 Logan International, terminal B
09:16 , terminal 3
3h 6m
Seasonal
Boeing 737-800

Days of the week are taken from the schedule for the next 14 days; schedules change by season. Chicago is 1 hour behind Boston. The search shows seat availability and the price for your date.

Airlines flying Boston to Chicago

Flights a week by schedule and the cheapest nonstop fare of each airline found by recent searches

American Airlines19 a week United Airlines14 a week Southwest Airlines9 a week Delta7 a week jetBluefrom 27 April

Airports

Where flights from Boston to Chicago depart and land

Departure from Boston

Logan International BOS

49 flights a week, terminals A, B, C, 2 mi (3 km) from the city centre

About the airport

Arrival in Chicago

Chicago Midway International MDW

9 flights a week, 9 mi (14 km) from the city centre

About the airport

When to visit Chicago

Weather by month

Best time to visit: May, June, July, August, September and October, +18° to +27° by day. In November it is +10° by day and +2° at night, with 7 rainy days.

Jan
0° −7° 10 days
Feb
+2° −6° 7 days
Mar
+9° 0° 12 days
Apr
+14° +5° 13 days
May
+19° +10° 11 days
Jun
+27° +17° 9 days
Jul
+27° +19° 12 days
Aug
+27° +19° 10 days
Sep
+24° +16° 7 days
Oct
+18° +10° 11 days
Nov
+10° +2° 7 days
Dec
+4° −3° 10 days

Daytime and night temperatures in °C, rainy days. Months with the most comfortable weather are in green. Long-term averages.

Frequently asked questions

How long is the flight from Boston to Chicago?
A nonstop flight takes 3 hours 3 minutes on average, from 2h 40m to 3h 22m depending on the flight.
How far is Chicago from Boston?
849 mi (1,366 km) in a straight line between the cities.
Which airlines fly nonstop from Boston to Chicago?
American Airlines (19 a week), United Airlines (14 a week), Southwest Airlines (9 a week), Delta (7 a week) and jetBlue.
How many flights a day are there from Boston to Chicago?
5 flights today and 49 a week, about 7 a day on average.
When are the first and last flights from Boston to Chicago?
The first departure is at 05:39 (AA421), the last at 07:45 (DL2570). Local time.
What is the cheapest month to fly from Boston to Chicago?
November 2026: tickets from $114. The most expensive is March 2027, from $183.
What is the cheapest upcoming date to fly from Boston to Chicago?
11 November 2026 (Wednesday): from $114 one way, nonstop, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Boston to Chicago?
American Airlines: nonstop tickets from $114 on 11 November by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Boston and Chicago?
Chicago is 1 hour behind Boston. Schedule times on this page are local to each airport.
Which Boston airport do flights to Chicago leave from?
Logan International (49 a week).