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Cheap flights Chicago to Boston (Logan)

1 passenger, economy

Nonstop flights from Chicago to Boston: American Airlines, United Airlines, Southwest Airlines and 1 more. Nonstop flights per week: 44. Flight time: 2 hours 29 minutes. Distance: 1389 km. Tickets from £68 (departure 18 November).

Prices updated on 8 November at 10:56

See also: Boston (Logan) — ChicagoFlights from ChicagoFlights to Boston (Logan)

Cheap flights Chicago to Boston

Compare prices, duration and stops

American Airlines
AA 1951
06:00
O'Hare International Airport (ORD)
Sun, 8 Nov
2h 29min
Direct
09:29
Logan (BOS)
Sun, 8 Nov
£111
Southwest Airlines
WN 4113
07:50
Chicago Midway International Airport (MDW)
Sun, 8 Nov
2h 20min
Direct
11:10
Logan (BOS)
Sun, 8 Nov
£117
Jetblue Airways
B6 1012
20:15
O'Hare International Airport (ORD)
Mon, 9 Nov
2h 44min
Direct
23:59
Logan (BOS)
Mon, 9 Nov
£78
American Airlines
AA 482
12:06
O'Hare International Airport (ORD)
Tue, 10 Nov
2h 30min
Direct
15:36
Logan (BOS)
Tue, 10 Nov
£118
Jetblue Airways
B6 112
13:00
O'Hare International Airport (ORD)
Thu, 12 Nov
2h 49min
Direct
16:49
Logan (BOS)
Thu, 12 Nov
£73
American Airlines
AA 469
17:52
O'Hare International Airport (ORD)
Thu, 12 Nov
2h 34min
Direct
21:26
Logan (BOS)
Thu, 12 Nov
£117
Allegiant Air
G4 1432
15:16
Chicago Midway International Airport (MDW)
Fri, 13 Nov
16h 3min
1 stop
08:19
Logan (BOS)
Sat, 14 Nov +1
£111
Southwest Airlines
WN 4113
07:40
Chicago Midway International Airport (MDW)
Sat, 14 Nov
2h 15min
Direct
10:55
Logan (BOS)
Sat, 14 Nov
£73
Jetblue Airways
B6 112
13:00
O'Hare International Airport (ORD)
Sat, 14 Nov
2h 49min
Direct
16:49
Logan (BOS)
Sat, 14 Nov
£131
American Airlines
AA 3067
06:59
O'Hare International Airport (ORD)
Sun, 15 Nov
2h 29min
Direct
10:28
Logan (BOS)
Sun, 15 Nov
£105
American Airlines
AA 1457
20:00
O'Hare International Airport (ORD)
Sun, 15 Nov
2h 31min
Direct
23:31
Logan (BOS)
Sun, 15 Nov
£125
American Airlines
AA 2074
13:37
O'Hare International Airport (ORD)
Tue, 17 Nov
2h 31min
Direct
17:08
Logan (BOS)
Tue, 17 Nov
£112
United Airlines
UA 2220
12:11
O'Hare International Airport (ORD)
Wed, 18 Nov
2h 25min
Direct
15:36
Logan (BOS)
Wed, 18 Nov
£121
American Airlines
AA 1457 🔥 Hot deal Best price
19:59
O'Hare International Airport (ORD)
Wed, 18 Nov
2h 28min
Direct
23:27
Logan (BOS)
Wed, 18 Nov
£68
Frontier Airlines
F9 1458
05:42
Chicago Midway International Airport (MDW)
Sat, 21 Nov
12h 29min
1 stop
19:11
Logan (BOS)
Sat, 21 Nov
£90
Jetblue Airways
B6 1012
02:30
O'Hare International Airport (ORD)
Sun, 22 Nov
2h 29min
Direct
05:59
Logan (BOS)
Sun, 22 Nov
£108
Frontier Airlines
F9 1458
20:42
Chicago Midway International Airport (MDW)
Sat, 21 Nov
12h 29min
1 stop
10:11
Logan (BOS)
Sun, 22 Nov +1
£80
Frontier Airlines
F9 1458
05:42
Chicago Midway International Airport (MDW)
Mon, 23 Nov
12h 29min
1 stop
19:11
Logan (BOS)
Mon, 23 Nov
£102
Southwest Airlines
WN 2902
03:45
Chicago Midway International Airport (MDW)
Tue, 24 Nov
2h 15min
Direct
07:00
Logan (BOS)
Tue, 24 Nov
£88
Southwest Airlines
WN 4113
07:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
2h 20min
Direct
11:05
Logan (BOS)
Thu, 26 Nov
£116
United Airlines
UA 1117
18:13
O'Hare International Airport (ORD)
Thu, 26 Nov
2h 33min
Direct
21:46
Logan (BOS)
Thu, 26 Nov
£108
United Airlines
UA 2331
03:08
O'Hare International Airport (ORD)
Sat, 28 Nov
2h 33min
Direct
06:41
Logan (BOS)
Sat, 28 Nov
£108
American Airlines
AA 1515
06:00
O'Hare International Airport (ORD)
Sat, 28 Nov
2h 24min
Direct
09:24
Logan (BOS)
Sat, 28 Nov
£193
United Airlines
UA 2213
07:00
O'Hare International Airport (ORD)
Sat, 28 Nov
2h 19min
Direct
10:19
Logan (BOS)
Sat, 28 Nov
£187
Southwest Airlines
WN 3014
05:35
Chicago Midway International Airport (MDW)
Sun, 29 Nov
2h 15min
Direct
08:50
Logan (BOS)
Sun, 29 Nov
£275
United Airlines
UA 1186
06:15
O'Hare International Airport (ORD)
Sun, 29 Nov
2h 19min
Direct
09:34
Logan (BOS)
Sun, 29 Nov
£242
Frontier Airlines
F9 1458
20:42
Chicago Midway International Airport (MDW)
Sun, 29 Nov
49h 56min
3 stops
23:38
Logan (BOS)
Tue, 1 Dec +1
£216
United Airlines
UA 2296
21:20
O'Hare International Airport (ORD)
Mon, 30 Nov
2h 25min
Direct
00:45
Logan (BOS)
Tue, 1 Dec +1
£137
Southwest Airlines
WN 4113
16:50
Chicago Midway International Airport (MDW)
Fri, 11 Dec
2h 20min
Direct
20:10
Logan (BOS)
Fri, 11 Dec
£95
Southwest Airlines
WN 4113
17:30
Chicago Midway International Airport (MDW)
Mon, 14 Dec
2h 30min
Direct
21:00
Logan (BOS)
Mon, 14 Dec
£85
Jetblue Airways
B6 1012
04:55
O'Hare International Airport (ORD)
Sat, 19 Dec
2h 26min
Direct
08:21
Logan (BOS)
Sat, 19 Dec
£117
United Airlines
UA 1707
06:20
O'Hare International Airport (ORD)
Sun, 20 Dec
2h 35min
Direct
09:55
Logan (BOS)
Sun, 20 Dec
£96
Frontier Airlines
F9 2198
18:19
O'Hare International Airport (ORD)
Sun, 20 Dec
12h 24min
1 stop
07:43
Logan (BOS)
Mon, 21 Dec +1
£104
Southwest Airlines
WN 2901
01:05
Chicago Midway International Airport (MDW)
Tue, 22 Dec
2h 15min
Direct
04:20
Logan (BOS)
Tue, 22 Dec
£94
Frontier Airlines
F9 2198
17:59
O'Hare International Airport (ORD)
Tue, 22 Dec
12h 44min
1 stop
07:43
Logan (BOS)
Wed, 23 Dec +1
£84
Frontier Airlines
F9 1458
20:35
Chicago Midway International Airport (MDW)
Tue, 22 Dec
11h 55min
1 stop
09:30
Logan (BOS)
Wed, 23 Dec +1
£81
United Airlines
UA 2213
15:50
O'Hare International Airport (ORD)
Wed, 23 Dec
2h 27min
Direct
19:17
Logan (BOS)
Wed, 23 Dec
£84
American Airlines
AA 4572
00:55
O'Hare International Airport (ORD)
Thu, 24 Dec
2h 40min
Direct
04:35
Logan (BOS)
Thu, 24 Dec
£111
American Airlines
AA 1457
18:00
O'Hare International Airport (ORD)
Thu, 24 Dec
2h 51min
Direct
21:51
Logan (BOS)
Thu, 24 Dec
£90
Southwest Airlines
WN 2902
18:25
Chicago Midway International Airport (MDW)
Fri, 25 Dec
2h 20min
Direct
21:45
Logan (BOS)
Fri, 25 Dec
£80
United Airlines
UA 2213
15:50
O'Hare International Airport (ORD)
Wed, 30 Dec
2h 27min
Direct
19:17
Logan (BOS)
Wed, 30 Dec
£91
Southwest Airlines
WN 4113
16:50
Chicago Midway International Airport (MDW)
Mon, 4 Jan
2h 20min
Direct
20:10
Logan (BOS)
Mon, 4 Jan
£117
Southwest Airlines
WN 4113
17:30
Chicago Midway International Airport (MDW)
Tue, 5 Jan
2h 30min
Direct
21:00
Logan (BOS)
Tue, 5 Jan
£110
American Airlines
AA 3797
06:00
O'Hare International Airport (ORD)
Wed, 24 Mar
2h 32min
Direct
09:32
Logan (BOS)
Wed, 24 Mar
£133
Jetblue Airways
B6 312
11:00
O'Hare International Airport (ORD)
Wed, 24 Mar
2h 24min
Direct
14:24
Logan (BOS)
Wed, 24 Mar
£133
Jetblue Airways
B6 312
14:30
O'Hare International Airport (ORD)
Wed, 24 Mar
2h 31min
Direct
18:01
Logan (BOS)
Wed, 24 Mar
£130
American Airlines
AA 1073
17:21
O'Hare International Airport (ORD)
Wed, 24 Mar
2h 31min
Direct
20:52
Logan (BOS)
Wed, 24 Mar
£138
Jetblue Airways
B6 312
19:00
O'Hare International Airport (ORD)
Mon, 19 Apr
2h 24min
Direct
22:24
Logan (BOS)
Mon, 19 Apr
£128
Jetblue Airways
B6 312
19:00
O'Hare International Airport (ORD)
Tue, 20 Apr
2h 24min
Direct
22:24
Logan (BOS)
Tue, 20 Apr
£128
United Airlines
UA 2331
02:00
O'Hare International Airport (ORD)
Wed, 5 May
2h 33min
Direct
05:33
Logan (BOS)
Wed, 5 May
£114

Direct flight schedule Chicago — Boston

Direct flights: 8 · Airlines: 4 · First departure: 02:00 · Last departure: 19:00

Departure → arrivalFlightAirport DaysDurationPrice
02:00→05:33 United Airlines UA 2331 O'HareORD MonTueWedThuFriSatSun 2h 33min
02:30→05:56 Jetblue Airways B6 1012 O'HareORD MonTueWedThuFriSatSun 2h 26min
03:45→07:00 Southwest Airlines WN 2902 Chicago MidwayMDW MonTueWedThuFriSatSun 2h 15min
13:00→16:49 Jetblue Airways B6 112 O'HareORD MonTueWedThuFriSatSun 2h 49min
15:50→19:17 United Airlines UA 2213 O'HareORD MonTueWedThuFriSatSun 2h 27min
16:50→20:10 Southwest Airlines WN 4113 Chicago MidwayMDW MonTueWedThuFriSatSun 2h 20min
18:00→21:28 American Airlines AA 1457 O'HareORD MonTueWedThuFriSatSun 2h 28min
19:00→22:24 Jetblue Airways B6 312 O'HareORD MonTueWedThuFriSatSun 2h 24min
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 Thu, 19 Nov · One way from £68

Prices as of 8 November, 11:10 Moscow time

Cheap flights Chicago to Boston

Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Sat, Sun
Price from
£78
Frontier Airlines
Frontier Airlines
Mon, Tue, Sat, Sun
Price from
£80
American Airlines
American Airlines
Mon, Tue, Wed, Thu, Sat, Sun
Price from
£105
Allegiant Air
Allegiant Air
Fri
Price from
£111
Southwest Airlines
Southwest Airlines
Mon, Tue, Thu, Fri, Sat, Sun
Price from
£117
United Airlines
United Airlines
Mon, Wed, Thu, Sat, Sun
Price from
£121

Which airlines offer the cheapest flights from Chicago to Boston?

Based on collected data, the cheapest flights are offered by Frontier Airlines with an average ticket price of £108.

  • Frontier Airlines Average price: £108 · Flights: 2 · Direct: 0
  • Allegiant Air Average price: £111 · Flights: 1 · Direct: 0
  • Southwest Airlines Average price: £114 · Flights: 4 · Direct: 4
  • Jetblue Airways Average price: £114 · Flights: 3 · Direct: 3
  • American Airlines Average price: £120 · Flights: 14 · Direct: 14
  • United Airlines Average price: £128 · Flights: 8 · Direct: 8

Which airlines fly most often from Chicago to Boston?

The most flight options on this route are offered by American Airlines — options found: 14.

  • American Airlines Flights: 14 · Direct: 14
  • United Airlines Flights: 8 · Direct: 8
  • Southwest Airlines Flights: 4 · Direct: 4
  • Jetblue Airways Flights: 3 · Direct: 3
  • Frontier Airlines Flights: 2 · Direct: 0
  • Allegiant Air Flights: 1 · Direct: 0

Round trip Chicago — Boston

TripOutboundReturnOutbound + returnTotal
Weekend tripFri, 11 DecMon, 14 Dec £95 + £87
One weekThu, 19 NovThu, 26 Nov £68 + £74
Two weeksSun, 22 NovMon, 7 Dec £80 + £76

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

Prices as of 8 November, 11:10 Moscow time

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

The cheapest departure right now is Thu, 19 Nov — from £68. Days before departure: 11. 4–7 days before departure tickets cost from £105, 1–3 days before — from £78.

Before departureDeparture dateDifference from lowestPrice
1–3 days Tue, 10 Nov 15% more
4–7 days Sun, 15 Nov 54% more
8–14 days Thu, 19 Nov cheapest
15–21 days Tue, 24 Nov 29% more
22–30 days Tue, 1 Dec 101% more

Lowest prices for departures in the next 30 days.

How many flights per day operate from Chicago to Boston?

Most flights operate on Sun (12), the fewest on Fri (3).

  • Mon Flights: 7 · Direct: 6
  • Tue Flights: 8 · Direct: 6
  • Wed Flights: 8 · Direct: 8
  • Thu Flights: 6 · Direct: 6
  • Fri Flights: 3 · Direct: 2
  • Sat Flights: 7 · Direct: 6
  • Sun Flights: 12 · Direct: 10

Popular destinations from Chicago

All →
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
£18
CHI
Chicago — Miami
United States → United States
MIA
from
£20
CHI
Chicago — Nashville
United States → United States
BNA
from
£29
CHI
Chicago — Phoenix
United States → United States
PHX
from
£40
CHI
Chicago — Denver
United States → United States
DEN
from
£40
CHI
Chicago — Atlanta
United States → United States
ATL
from
£42
CHI
Chicago — Orlando
United States → United States
ORL
from
£48

Popular destinations to Boston

All →
WAS
Washington — Boston
United States → United States
BOS
from
£41
ORL
Orlando — Boston
United States → United States
BOS
from
£45
NYC
New York — Boston
United States → United States
BOS
from
£66
PHL
Philadelphia — Boston
United States → United States
BOS
from
£73
SAN
San Diego — Boston
United States → United States
BOS
from
£74
DEN
Denver — Boston
United States → United States
BOS
from
£75
CLT
Charlotte — Boston
United States → United States
BOS
from
£83
BWI
Baltimore — Boston
United States → United States
BOS
from
£86

Flights from Chicago to cities near Boston

Flights to Boston are currently cheaper than to nearby cities: from £68.

City Distance Direct Flights Airlines Price from
BostonBOS — 27306
ProvidencePVD 78 km 111
PortlandPWM 153 km 011

Distance is a straight line between the cities. Prices are the lowest one-way fares.

Cheap flights Chicago to Boston

Price from
£68
Average price
£111
Flight time
2 hours 29 minutes
Distance
1 389 km
Рейсов в неделю
44
Airlines
6
Most frequent flight
AA 1457

Prices as of 8 November, 10:56 Moscow time

Airports on the Chicago — Boston route

From → to Flights Direct Airlines Price from
O'Hare International AirportORD LoganBOS Cheapest
24234
Chicago Midway International AirportMDW LoganBOS
643

Departure airports · Chicago

Arrival airports · Boston

Passenger reviews

No reviews for this route yet

Internet abroad

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Frequently Asked Questions

Yes. Nonstop flights from Chicago to Boston are operated by: American Airlines, United Airlines, Southwest Airlines, Jetblue Airways. A nonstop flight takes 2 hours 29 minutes on average. Nonstop tickets start at £68.
The average ticket price Chicago Boston is £111. The cheapest ticket costs £68, operated by American Airlines, flight AA 1457, departing Chicago on 18 November at 19:59, arriving Boston on 18 November at 23:27. Prices as of 8 November.
A nonstop flight takes 2 hours 29 minutes on average. The fastest is WN 4113 Southwest Airlines: 2 hours 15 minutes. With a connection: from 11 hours 55 minutes, usually about 12 hours.
Flights from Chicago to Boston depart from these airports: O'Hare International Airport (ORD), Chicago Midway International Airport (MDW). Most flights depart from O'Hare International Airport. Arrival: Logan (BOS).
Based on prices for the coming months, the cheapest month to fly is November: tickets from £68. The most expensive month is December, with tickets from £80.
Tickets from Chicago to Boston are sold by: American Airlines, United Airlines, Southwest Airlines, Jetblue Airways, Frontier Airlines, Allegiant Air. Nonstop: American Airlines, United Airlines, Southwest Airlines, Jetblue Airways.
The distance from Chicago to Boston is 1389 km.
Tickets from Boston to Chicago start at £64. The average price is £106. Nonstop flights are operated by: American Airlines, Southwest Airlines, Jetblue Airways, United Airlines. All tickets Boston — Chicago