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Cheap flights Boston (Logan) to Chicago

1 passenger, economy

Nonstop flights from Boston to Chicago: American Airlines, Southwest Airlines, Jetblue Airways and 1 more. Nonstop flights per week: 55. Flight time: 3 hours 4 minutes. Distance: 1389 km. Tickets from 76 € (departure 26 November).

Prices updated on 20 October at 11:10

See also: Chicago — Boston (Logan)Flights from Boston (Logan)Flights to Chicago

Cheap flights Boston to Chicago

Compare prices, duration and stops

American Airlines
AA 3324
05:54
Logan (BOS)
Wed, 21 Oct
3h 6min
Direct
08:00
O'Hare International Airport (ORD)
Wed, 21 Oct
149 €
Frontier Airlines
F9 3511
12:57
Logan (BOS)
Wed, 21 Oct
6h 34min
1 stop
18:31
O'Hare International Airport (ORD)
Wed, 21 Oct
102 €
Jetblue Airways
B6 811
00:12
Logan (BOS)
Thu, 22 Oct
3h 2min
Direct
02:14
O'Hare International Airport (ORD)
Thu, 22 Oct
86 €
Southwest Airlines
WN 909
22:00
Logan (BOS)
Thu, 22 Oct
2h 40min
Direct
23:40
Chicago Midway International Airport (MDW)
Thu, 22 Oct
110 €
Frontier Airlines
F9 3511
12:57
Logan (BOS)
Fri, 23 Oct
11h 46min
1 stop
23:43
Chicago Midway International Airport (MDW)
Fri, 23 Oct
132 €
American Airlines
AA 3160
18:16
Logan (BOS)
Fri, 23 Oct
3h 12min
Direct
20:28
O'Hare International Airport (ORD)
Fri, 23 Oct
142 €
Southwest Airlines
WN 1346
16:40
Logan (BOS)
Sat, 24 Oct
2h 35min
Direct
18:15
Chicago Midway International Airport (MDW)
Sat, 24 Oct
101 €
Frontier Airlines
F9 3511
11:42
Logan (BOS)
Sat, 24 Oct
7h 49min
1 stop
18:31
O'Hare International Airport (ORD)
Sat, 24 Oct
135 €
American Airlines
AA 3324
12:54
Logan (BOS)
Sun, 25 Oct
3h 6min
Direct
15:00
O'Hare International Airport (ORD)
Sun, 25 Oct
143 €
Southwest Airlines
WN 805
12:50
Logan (BOS)
Mon, 26 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Mon, 26 Oct
101 €
Frontier Airlines
F9 3511
12:57
Logan (BOS)
Mon, 26 Oct
11h 46min
1 stop
23:43
Chicago Midway International Airport (MDW)
Mon, 26 Oct
129 €
Jetblue Airways
B6 111
16:59
Logan (BOS)
Tue, 27 Oct
3h 1min
Direct
19:00
O'Hare International Airport (ORD)
Tue, 27 Oct
88 €
Frontier Airlines
F9 3511
11:12
Logan (BOS)
Tue, 27 Oct
8h 33min
1 stop
18:45
O'Hare International Airport (ORD)
Tue, 27 Oct
112 €
Jetblue Airways
B6 811
00:15
Logan (BOS)
Wed, 28 Oct
3h 14min
Direct
02:29
O'Hare International Airport (ORD)
Wed, 28 Oct
98 €
Jetblue Airways
B6 111
16:59
Logan (BOS)
Wed, 28 Oct
3h 1min
Direct
19:00
O'Hare International Airport (ORD)
Wed, 28 Oct
88 €
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Wed, 28 Oct
6h 37min
1 stop
18:16
O'Hare International Airport (ORD)
Wed, 28 Oct
124 €
Southwest Airlines
WN 807
12:50
Logan (BOS)
Wed, 28 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Wed, 28 Oct
135 €
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Thu, 29 Oct
12h 8min
1 stop
23:47
Chicago Midway International Airport (MDW)
Thu, 29 Oct
138 €
United Airlines
UA 375
20:29
Logan (BOS)
Thu, 29 Oct
3h 3min
Direct
22:32
O'Hare International Airport (ORD)
Thu, 29 Oct
97 €
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Fri, 30 Oct
7h 6min
1 stop
18:45
O'Hare International Airport (ORD)
Fri, 30 Oct
112 €
Frontier Airlines
F9 3511
11:27
Logan (BOS)
Sat, 31 Oct
7h 49min
1 stop
18:16
O'Hare International Airport (ORD)
Sat, 31 Oct
109 €
American Airlines
AA 2146
05:43
Logan (BOS)
Sun, 1 Nov
3h 17min
Direct
08:00
O'Hare International Airport (ORD)
Sun, 1 Nov
155 €
American Airlines
AA 947
07:13
Logan (BOS)
Sun, 1 Nov
3h 16min
Direct
09:29
O'Hare International Airport (ORD)
Sun, 1 Nov
153 €
Jetblue Airways
B6 111
17:59
Logan (BOS)
Sun, 1 Nov
3h
Direct
19:59
O'Hare International Airport (ORD)
Sun, 1 Nov
157 €
American Airlines
AA 1951
18:19
Logan (BOS)
Sun, 1 Nov
3h 10min
Direct
20:29
O'Hare International Airport (ORD)
Sun, 1 Nov
113 €
Jetblue Airways
B6 111
17:59
Logan (BOS)
Mon, 2 Nov
3h 1min
Direct
20:00
O'Hare International Airport (ORD)
Mon, 2 Nov
133 €
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Mon, 2 Nov
7h 6min
1 stop
18:45
O'Hare International Airport (ORD)
Mon, 2 Nov
132 €
Jetblue Airways
B6 811
17:05
Logan (BOS)
Mon, 2 Nov
3h 12min
Direct
19:17
O'Hare International Airport (ORD)
Mon, 2 Nov
80 €
American Airlines
AA 2925
03:40
Logan (BOS)
Tue, 3 Nov
3h 14min
Direct
05:54
O'Hare International Airport (ORD)
Tue, 3 Nov
101 €
American Airlines
AA 2146
13:43
Logan (BOS)
Tue, 3 Nov
3h 17min
Direct
16:00
O'Hare International Airport (ORD)
Tue, 3 Nov
101 €
Frontier Airlines
F9 3511
12:15
Logan (BOS)
Tue, 3 Nov
7h 15min
1 stop
18:30
O'Hare International Airport (ORD)
Tue, 3 Nov
118 €
Southwest Airlines
WN 816 🔥 Hot deal
17:55
Logan (BOS)
Tue, 3 Nov
2h 45min
Direct
19:40
Chicago Midway International Airport (MDW)
Tue, 3 Nov
95 €
Jetblue Airways
B6 111 🔥 Hot deal
09:59
Logan (BOS)
Wed, 4 Nov
3h 1min
Direct
12:00
O'Hare International Airport (ORD)
Wed, 4 Nov
79 €
American Airlines
AA 894
20:33
Logan (BOS)
Wed, 4 Nov
3h 7min
Direct
22:40
O'Hare International Airport (ORD)
Wed, 4 Nov
142 €
Jetblue Airways
B6 111
17:59
Logan (BOS)
Thu, 5 Nov
3h
Direct
19:59
O'Hare International Airport (ORD)
Thu, 5 Nov
104 €
United Airlines
UA 1732
19:55
Logan (BOS)
Thu, 5 Nov
3h 4min
Direct
21:59
O'Hare International Airport (ORD)
Thu, 5 Nov
85 €
Jetblue Airways
B6 811
17:05
Logan (BOS)
Fri, 6 Nov
3h 12min
Direct
19:17
O'Hare International Airport (ORD)
Fri, 6 Nov
123 €
Southwest Airlines
WN 816
02:30
Logan (BOS)
Sat, 7 Nov
2h 45min
Direct
04:15
Chicago Midway International Airport (MDW)
Sat, 7 Nov
114 €
American Airlines
AA 2166
18:20
Logan (BOS)
Sat, 7 Nov
3h 9min
Direct
20:29
O'Hare International Airport (ORD)
Sat, 7 Nov
101 €
United Airlines
UA 1414
14:00
Logan (BOS)
Mon, 9 Nov
3h
Direct
16:00
O'Hare International Airport (ORD)
Mon, 9 Nov
86 €
Jetblue Airways
B6 111
19:15
Logan (BOS)
Mon, 9 Nov
3h 5min
Direct
21:20
O'Hare International Airport (ORD)
Mon, 9 Nov
118 €
Jetblue Airways
B6 811
17:05
Logan (BOS)
Mon, 9 Nov
3h 12min
Direct
19:17
O'Hare International Airport (ORD)
Mon, 9 Nov
79 €
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Fri, 13 Nov
7h 6min
1 stop
02:45
O'Hare International Airport (ORD)
Sat, 14 Nov +1
129 €
Southwest Airlines
WN 2758
15:10
Logan (BOS)
Sat, 14 Nov
2h 45min
Direct
16:55
Chicago Midway International Airport (MDW)
Sat, 14 Nov
87 €
Frontier Airlines
F9 3511
20:15
Logan (BOS)
Tue, 17 Nov
6h 32min
1 stop
01:47
Chicago Midway International Airport (MDW)
Wed, 18 Nov +1
120 €
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Wed, 18 Nov
6h 37min
1 stop
02:16
O'Hare International Airport (ORD)
Thu, 19 Nov +1
120 €
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Thu, 19 Nov
7h 6min
1 stop
02:45
O'Hare International Airport (ORD)
Fri, 20 Nov +1
120 €
American Airlines
AA 751 Best price
20:08
Logan (BOS)
Thu, 26 Nov
3h 12min
Direct
22:20
O'Hare International Airport (ORD)
Thu, 26 Nov
76 €
Southwest Airlines
WN 0813
13:05
Logan (BOS)
Thu, 26 Nov
2h 40min
Direct
14:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
88 €
Southwest Airlines
WN 2185
07:05
Logan (BOS)
Fri, 27 Nov
2h 45min
Direct
08:50
Chicago Midway International Airport (MDW)
Fri, 27 Nov
138 €

Direct flight schedule Boston — Chicago

Direct flights: 11 · Airlines: 4 · First departure: 05:43 · Last departure: 20:29

Departure → arrivalFlightAirport DaysDurationPrice
05:43→08:00 American Airlines AA 2146 LoganBOS MonTueWedThuFriSatSun 3h 17min
07:05→08:50 Southwest Airlines WN 2185 LoganBOS MonTueWedThuFriSatSun 2h 45min
07:13→09:26 American Airlines AA 947 LoganBOS MonTueWedThuFriSatSun 3h 13min
08:00→10:10 Jetblue Airways B6 311 LoganBOS MonTueWedThuFriSatSun 3h 10min
12:45→14:30 Southwest Airlines WN 813 LoganBOS MonTueWedThuFriSatSun 2h 45min
13:45→15:51 United Airlines UA 1414 LoganBOS MonTueWedThuFriSatSun 3h 6min
15:10→16:55 Southwest Airlines WN 2758 LoganBOS MonTueWedThuFriSatSun 2h 45min
17:05→19:07 Jetblue Airways B6 811 LoganBOS MonTueWedThuFriSatSun 3h 2min
Local time: departure at the departure airport, arrival at the arrival airport. Days and prices are based on tickets found for the coming months.

Low price calendar

From
To
Lowest price of the month Sat, 31 Oct · One way from 109 €

Prices as of 20 October, 11:11 Moscow time

Cheap flights Boston to Chicago

Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri, Sun
Price from
79 €
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
87 €
Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat
Price from
91 €
American Airlines
American Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
142 €
United Airlines
United Airlines
Mon, Tue, Wed, Thu, Fri, Sat
Price from
153 €

Which airlines offer the cheapest flights from Boston to Chicago?

Based on collected data, the cheapest flights are offered by Southwest Airlines with an average ticket price of 114 €.

  • Southwest Airlines Average price: 114 € · Flights: 10 · Direct: 10
  • Jetblue Airways Average price: 116 € · Flights: 3 · Direct: 3
  • United Airlines Average price: 120 € · Flights: 3 · Direct: 3
  • Frontier Airlines Average price: 121 € · Flights: 3 · Direct: 0
  • American Airlines Average price: 127 € · Flights: 16 · Direct: 16

Which airlines fly most often from Boston to Chicago?

The most flight options on this route are offered by American Airlines — options found: 16.

  • American Airlines Flights: 16 · Direct: 16
  • Southwest Airlines Flights: 10 · Direct: 10
  • Jetblue Airways Flights: 3 · Direct: 3
  • United Airlines Flights: 3 · Direct: 3
  • Frontier Airlines Flights: 3 · Direct: 0

Round trip Boston — Chicago

TripOutboundReturnOutbound + returnTotal
Weekend tripSat, 12 DecMon, 14 Dec 93 € + 102 €
One weekWed, 4 NovThu, 12 Nov 79 € + 87 €
Two weeksWed, 4 NovThu, 19 Nov 79 € + 81 €

Two one-way tickets combined, price per adult. Tap a price to search these dates.

Prices as of 20 October, 11:11 Moscow time

How many days before departure is it cheapest to buy a Boston — Chicago ticket?

The cheapest departure right now is Wed, 4 Nov — from 79 €. Days before departure: 14. 4–7 days before departure tickets cost from 112 €, 1–3 days before — from 132 €.

Before departureDeparture dateDifference from lowestPrice
1–3 days Fri, 23 Oct 67% more
4–7 days Tue, 27 Oct 41% more
8–14 days Wed, 4 Nov cheapest
15–21 days Mon, 9 Nov cheapest
22–30 days Sat, 14 Nov 10% more

Lowest prices for departures in the next 30 days.

How many flights per day operate from Boston to Chicago?

Most flights operate on Thu (13), the fewest on Sat (6).

  • Mon Flights: 11 · Direct: 9
  • Tue Flights: 10 · Direct: 9
  • Wed Flights: 12 · Direct: 11
  • Thu Flights: 13 · Direct: 11
  • Fri Flights: 7 · Direct: 5
  • Sat Flights: 6 · Direct: 5
  • Sun Flights: 6 · Direct: 6

Popular destinations from Boston

All →
BOS
Boston — Baltimore
United States → United States
BWI
from
50 €
BOS
Boston — Washington
United States → United States
WAS
from
53 €
BOS
Boston — Lebanon
United States → United States
LEB
from
59 €
BOS
Boston — Fort Lauderdale
United States → United States
FLL
from
62 €
BOS
Boston — Miami
United States → United States
MIA
from
69 €
BOS
Boston — Rutland
United States → United States
RUT
from
72 €

Popular destinations to Chicago

All →
FLL
Fort Lauderdale — Chicago
United States → United States
CHI
from
28 €
ATL
Atlanta — Chicago
United States → United States
CHI
from
40 €
TPA
Tampa — Chicago
United States → United States
CHI
from
47 €
DEN
Denver — Chicago
United States → United States
CHI
from
72 €
LAS
Las Vegas — Chicago
United States → United States
CHI
from
74 €
NYC
New York — Chicago
United States → United States
CHI
from
77 €
SAN
San Diego — Chicago
United States → United States
CHI
from
83 €
SFO
San Francisco — Chicago
United States → United States
CHI
from
91 €

Cheap flights Boston to Chicago

Price from
79 €
Average price
120 €
Flight time
3 hours 4 minutes
Distance
1 389 km
Рейсов в неделю
55
Airlines
5
Most frequent flight
B6 811

Prices as of 20 October, 11:10 Moscow time

Airports on the Boston — Chicago route

From → to Flights Direct Airlines Price from
LoganBOS O'Hare International AirportORD Cheapest
24224
LoganBOS Chicago Midway International AirportMDW
1192

Departure airports · Boston

Arrival airports · Chicago

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

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3 GB

data

30

days

8 €

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2 GB

data

15

days

11 €

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5 GB

data

30

days

12 €

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3 GB

data

30

days

14 €

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5 GB

data

30

days

20 €

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Frequently Asked Questions

Yes. Nonstop flights from Boston to Chicago are operated by: American Airlines, Southwest Airlines, Jetblue Airways, United Airlines. A nonstop flight takes 3 hours 4 minutes on average. Nonstop tickets start at 76 €.
The average ticket price Boston Chicago is 120 €. The cheapest ticket costs 76 €, operated by American Airlines, flight AA 751, departing Boston on 26 November at 20:08, arriving Chicago on 26 November at 22:20. Prices as of 20 October.
A nonstop flight takes 3 hours 4 minutes on average. The fastest is WN 1346 Southwest Airlines: 2 hours 35 minutes. With a connection: from 6 hours 32 minutes, usually about 7 hours.
Flights from Boston to Chicago arrive at these airports: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW). Most flights arrive at O'Hare International Airport. Departure: Logan (BOS).
Based on prices for the coming months, the cheapest month to fly is November: tickets from 79 €. The most expensive month is October, with tickets from 109 €.
Tickets from Boston to Chicago are sold by: American Airlines, Southwest Airlines, Jetblue Airways, Frontier Airlines, United Airlines. Nonstop: American Airlines, Southwest Airlines, Jetblue Airways, United Airlines.
The distance from Boston to Chicago is 1389 km.
Tickets from Chicago to Boston start at 79 €. The average price is 129 €. Nonstop flights are operated by: American Airlines, United Airlines, Southwest Airlines, Jetblue Airways. All tickets Chicago — Boston