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Cheap flights from Chicago to Boston

48 nonstop flights a week, 5 of them today. Operated by 4 airlines, about 2h 26m in the air, 849 mi (1,366 km). Tickets from $143, nonstop from $125.

Flights from Chicago to Boston

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: Chicago to Boston

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 Chicago to Boston

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

Cheapest one-way $113 22 December 2026, with a connection Cheapest nonstop $125 22 December 2026, B6 Cheapest in the next 7 days $142 15 November, Sun Cheapest weekend departure $143 Sat, 14 November 2026
Cheapest day of the week Sunday $229 on average over the next 120 days
Cheapest month December 2026 tickets from $113

Chicago to Boston at a glance

flight time, from 2h 10m to 2h 43m
2h 26m
straight-line distance
849 mi (1,366 km)
flights a week
48
flights today
5
first and last departure
06:00 - 07:50
lowest price, with a connection, 21 November
$143
lowest nonstop price
$125
airlines
4

Chicago to Boston ticket prices by month

Lowest one-way fare found by recent searches

Cheapest month: December 2026, tickets from $113. Prices come from searches over the last few days; check the search for your exact date.

The most expensive month is March 2027: from $179. The average across months is $144.

Chicago to Boston flight schedule

48 flights a week, 5 today, 50 seasonal or one-off. Departure and arrival times are local.

FlightDepartsArrivesDurationDaysAircraft
AA 1515
American Airlines
06:00 , terminal 3
09:24 Logan International, terminal B
2h 24m
Mon, Thu, Fri, Sat, Sun
Boeing 737-800
AA 1951
American Airlines
06:00 , terminal 3
09:29 Logan International, terminal B
2h 29m
Daily
Boeing 737-800
UA 1186
United Airlines
06:00 , terminal 1
09:19 Logan International, terminal B
2h 19m
Tue
Boeing 737
UA 1186
United Airlines
06:05 , terminal 1
09:23 Logan International, terminal B
2h 18m
Mon, Thu
Boeing 737
UA 1186
United Airlines
06:15 , terminal 1
09:34 Logan International, terminal B
2h 19m
Fri, Sun
Boeing 737
AA 981
American Airlines
06:58 , terminal 3
10:22 Logan International, terminal B
2h 24m
Mon
Boeing 737-800
AA 3067
American Airlines
06:59 , terminal 3
10:28 Logan International, terminal B
2h 29m
Daily
Boeing 737-800
AA 981
American Airlines
06:59 , terminal 3
10:22 Logan International, terminal B
2h 23m
Thu, Fri, Sat, Sun
Boeing 737-800
UA 2213
United Airlines
06:59 , terminal 1
10:18 Logan International, terminal B
2h 19m
Mon, Wed, Thu, Fri, Sat, Sun
Airbus A320
UA 2213
United Airlines
07:00 , terminal 1
10:19 Logan International, terminal B
2h 19m
Tue
Airbus A320
DL 2828
Delta
07:05 , terminal 5
10:32 Logan International, terminal A
2h 27m
Daily
Boeing 737-800
WN 4113
Southwest Airlines
07:40 Chicago Midway International
10:55 Logan International, terminal B
2h 15m
Sat
Boeing 737-800
WN 4113
Southwest Airlines
07:50 Chicago Midway International
11:10 Logan International, terminal B
2h 20m
Mon, Thu, Fri, Sun

Seasonal and one-off flights

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

FlightDepartsArrivesDurationDaysAircraft
WN 4113
Southwest Airlines
07:45 Chicago Midway International
11:00 Logan International, terminal B
2h 15m
Seasonal
Boeing 737-800
WN 3014
Southwest Airlines
05:35 Chicago Midway International
08:50 Logan International, terminal B
2h 15m
Seasonal
UA 2402
United Airlines
07:05 , terminal 1
10:31 Logan International, terminal B
2h 26m
Seasonal
Airbus A320
AA 640
American Airlines
06:00 , terminal 3
09:33 Logan International, terminal B
2h 33m
Seasonal
Boeing 737-800
AA 2089
American Airlines
06:59 , terminal 3
10:32 Logan International, terminal B
2h 33m
Seasonal
Boeing 737-800
AA 2239
American Airlines
08:05 , terminal 3
11:38 Logan International, terminal B
2h 33m
Seasonal
Boeing 737-800
UA 2213
United Airlines
06:50 , terminal 1
10:17 Logan International, terminal B
2h 27m
Seasonal
Airbus A320
AA 4398
American Airlines
05:44 , terminal 3
09:19 Logan International, terminal B
2h 35m
Seasonal
Embraer EMB 175
AA 4398
American Airlines
06:00 , terminal 3
09:35 Logan International, terminal B
2h 35m
Seasonal
Embraer EMB 175
DL 5688
Delta
07:05 , terminal 5
10:33 Logan International, terminal A
2h 28m
Seasonal
Embraer EMB 175
AA 4398
American Airlines
05:59 , terminal 3
09:34 Logan International, terminal B
2h 35m
Seasonal
Embraer EMB 175
DL 5688
Delta
08:05 , terminal 5
11:38 Logan International, terminal A
2h 33m
Seasonal
Embraer EMB 175
DL 5612
Delta
07:00 , terminal 5
10:28 Logan International, terminal A
2h 28m
Seasonal
Embraer EMB 175
UA 2603
United Airlines
07:15 , terminal 1
10:42 Logan International, terminal B
2h 27m
Seasonal
Boeing 737
AA 3797
American Airlines
06:00 , terminal 3
09:33 Logan International, terminal B
2h 33m
Seasonal
Embraer 170
AA 3092
American Airlines
06:47 , terminal 3
10:14 Logan International, terminal B
2h 27m
Seasonal
Boeing 737-800
AA 4685
American Airlines
08:00 , terminal 3
11:43 Logan International, terminal B
2h 43m
Seasonal
Embraer EMB 175
AA 3092
American Airlines
07:00 , terminal 3
10:27 Logan International, terminal B
2h 27m
Seasonal
Boeing 737-800
UA 2603
United Airlines
07:10 , terminal 1
10:38 Logan International, terminal B
2h 28m
Seasonal
Airbus A320
AA 4685
American Airlines
07:45 , terminal 3
11:28 Logan International, terminal B
2h 43m
Seasonal
Embraer EMB 175
AA 3067
American Airlines
07:00 , terminal 3
10:26 Logan International, terminal B
2h 26m
Seasonal
Boeing 737-800
UA 2318
United Airlines
07:25 , terminal 1
10:48 Logan International, terminal B
2h 23m
Seasonal
Boeing 737-800
WN 2631
Southwest Airlines
07:35 Chicago Midway International
10:50 Logan International, terminal B
2h 15m
Seasonal
Boeing 737
AA 4757
American Airlines
08:05 , terminal 3
11:38 Logan International, terminal B
2h 33m
Seasonal
Embraer EMB 175
WN 2631
Southwest Airlines
07:50 Chicago Midway International
11:10 Logan International, terminal B
2h 20m
Seasonal
AA 2805
American Airlines
07:00 , terminal 3
10:26 Logan International, terminal B
2h 26m
Seasonal
Boeing 737-800
AA 4629
American Airlines
08:05 , terminal 3
11:38 Logan International, terminal B
2h 33m
Seasonal
Embraer EMB 175
WN 2830
Southwest Airlines
07:50 Chicago Midway International
11:05 Logan International, terminal B
2h 15m
Seasonal
Boeing 737
WN 3784
Southwest Airlines
07:35 Chicago Midway International
10:45 Logan International, terminal B
2h 10m
Seasonal
WN 2830
Southwest Airlines
08:00 Chicago Midway International
11:15 Logan International, terminal B
2h 15m
Seasonal
UA 2394
United Airlines
06:00 , terminal 1
09:24 Logan International, terminal B
2h 24m
Seasonal
Boeing 737-800
UA 2318
United Airlines
07:30 , terminal 1
10:53 Logan International, terminal B
2h 23m
Seasonal
Boeing 737
AA 966
American Airlines
06:00 , terminal 3
09:27 Logan International, terminal B
2h 27m
Seasonal
Boeing 737-800
AA 4616
American Airlines
07:05 , terminal 3
10:39 Logan International, terminal B
2h 34m
Seasonal
Embraer EMB 175
WN 4625
Southwest Airlines
07:40 Chicago Midway International
10:55 Logan International, terminal B
2h 15m
Seasonal
AA 1759
American Airlines
08:05 , terminal 3
11:32 Logan International, terminal B
2h 27m
Seasonal
Boeing 737-800
WN 4625
Southwest Airlines
07:35 Chicago Midway International
10:50 Logan International, terminal B
2h 15m
Seasonal
Boeing 737
WN 4625
Southwest Airlines
07:55 Chicago Midway International
11:10 Logan International, terminal B
2h 15m
Seasonal
Boeing 737
WN 366
Southwest Airlines
07:35 Chicago Midway International
10:50 Logan International, terminal B
2h 15m
Seasonal
Boeing 737-800
DL 2828
Delta
07:00 , terminal 5
10:28 Logan International, terminal A
2h 28m
Seasonal
Airbus A220-300
AA 1759
American Airlines
07:00 , terminal 3
10:29 Logan International, terminal B
2h 29m
Seasonal
Boeing 737-800
AA 966
American Airlines
06:04 , terminal 3
09:30 Logan International, terminal B
2h 26m
Seasonal
Boeing 737-800
AA 592
American Airlines
07:00 , terminal 3
10:26 Logan International, terminal B
2h 26m
Seasonal
Boeing 737-800
WN 139
Southwest Airlines
07:15 Chicago Midway International
10:35 Logan International, terminal B
2h 20m
Seasonal
Boeing 737
WN 2404
Southwest Airlines
07:05 Chicago Midway International
10:25 Logan International, terminal B
2h 20m
Seasonal
Boeing 737
WN 3006
Southwest Airlines
07:50 Chicago Midway International
11:10 Logan International, terminal B
2h 20m
Seasonal
Boeing 737
WN 139
Southwest Airlines
05:40 Chicago Midway International
08:55 Logan International, terminal B
2h 15m
Seasonal
WN 2865
Southwest Airlines
07:55 Chicago Midway International
11:15 Logan International, terminal B
2h 20m
Seasonal
Boeing 737
AA 592
American Airlines
06:54 , terminal 3
10:28 Logan International, terminal B
2h 34m
Seasonal
Boeing 737-800
AA 966
American Airlines
06:05 , terminal 3
09:37 Logan International, terminal B
2h 32m
Seasonal
Boeing 737-800

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

Airlines flying Chicago to Boston

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

American Airlines24 a week United Airlines12 a week Delta7 a week Southwest Airlines5 a week

Airports

Where flights from Chicago to Boston depart and land

Departure from Chicago

Chicago Midway International MDW

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

About the airport

Arrival in Boston

Logan International BOS

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

About the airport

Frequently asked questions

How long is the flight from Chicago to Boston?
A nonstop flight takes 2 hours 26 minutes on average, from 2h 10m to 2h 43m depending on the flight.
How far is Boston from Chicago?
849 mi (1,366 km) in a straight line between the cities.
Which airlines fly nonstop from Chicago to Boston?
American Airlines (24 a week), United Airlines (12 a week), Delta (7 a week) and Southwest Airlines (5 a week).
How many flights a day are there from Chicago to Boston?
5 flights today and 48 a week, about 6.9 a day on average.
When are the first and last flights from Chicago to Boston?
The first departure is at 06:00 (AA1515), the last at 07:50 (WN4113). Local time.
What is the cheapest month to fly from Chicago to Boston?
December 2026: tickets from $113. The most expensive is March 2027, from $179.
What is the cheapest upcoming date to fly from Chicago to Boston?
22 December 2026 (Tuesday): from $113 one way, with a connection, by recent searches. The search shows the price for your dates.
Which airline is the cheapest from Chicago to Boston?
Southwest Airlines: nonstop tickets from $132 on 23 December by recent searches. Prices change daily, so compare the sellers in the search.
What is the time difference between Chicago and Boston?
Boston is 1 hour ahead of Chicago. Schedule times on this page are local to each airport.
Which Chicago airport do flights to Boston leave from?
Chicago Midway International (5 a week).