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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 28 minutes. Distance: 1389 km. Tickets from KSh11 218 (departure 4 November).

Prices updated on 20 October at 11:10

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

Cheap flights Chicago to Boston

Compare prices, duration and stops

Jetblue Airways
B6 1012
20:04
Chicago O'Hare International Airport (ORD)
Thu, 22 Oct
2h 55min
Direct
23:59
Logan (BOS)
Thu, 22 Oct
KSh15 621
Jetblue Airways
B6 1012
20:00
Chicago O'Hare International Airport (ORD)
Fri, 23 Oct
2h 59min
Direct
23:59
Logan (BOS)
Fri, 23 Oct
KSh19 379
American Airlines
AA 2950
14:00
Chicago O'Hare International Airport (ORD)
Sun, 25 Oct
2h 37min
Direct
17:37
Logan (BOS)
Sun, 25 Oct
KSh18 596
Southwest Airlines
WN 4535
15:50
Chicago Midway International Airport (MDW)
Mon, 26 Oct
2h 20min
Direct
19:10
Logan (BOS)
Mon, 26 Oct
KSh14 233
Jetblue Airways
B6 1012
04:24
Chicago O'Hare International Airport (ORD)
Tue, 27 Oct
2h 44min
Direct
08:08
Logan (BOS)
Tue, 27 Oct
KSh14 272
United Airlines
UA 2296
05:20
Chicago O'Hare International Airport (ORD)
Tue, 27 Oct
2h 26min
Direct
08:46
Logan (BOS)
Tue, 27 Oct
KSh18 221
United Airlines
UA 1186
14:00
Chicago O'Hare International Airport (ORD)
Tue, 27 Oct
2h 19min
Direct
17:19
Logan (BOS)
Tue, 27 Oct
KSh18 221
Southwest Airlines
WN 1266
02:10
Chicago Midway International Airport (MDW)
Wed, 28 Oct
2h 20min
Direct
05:30
Logan (BOS)
Wed, 28 Oct
KSh13 897
Jetblue Airways
B6 1012
04:24
Chicago O'Hare International Airport (ORD)
Wed, 28 Oct
2h 44min
Direct
08:08
Logan (BOS)
Wed, 28 Oct
KSh12 432
American Airlines
AA 1479
12:06
Chicago O'Hare International Airport (ORD)
Wed, 28 Oct
2h 43min
Direct
15:49
Logan (BOS)
Wed, 28 Oct
KSh19 508
Allegiant Air
G4 3054
14:26
Chicago Midway International Airport (MDW)
Fri, 30 Oct
16h 46min
1 stop
08:12
Logan (BOS)
Sat, 31 Oct +1
KSh19 328
Southwest Airlines
WN 2213
15:30
Chicago Midway International Airport (MDW)
Fri, 30 Oct
2h 20min
Direct
18:50
Logan (BOS)
Fri, 30 Oct
KSh20 723
Southwest Airlines
WN 4113
07:50
Chicago Midway International Airport (MDW)
Sun, 1 Nov
2h 20min
Direct
11:10
Logan (BOS)
Sun, 1 Nov
KSh20 778
Jetblue Airways
B6 1012
20:15
Chicago O'Hare International Airport (ORD)
Sun, 1 Nov
2h 44min
Direct
23:59
Logan (BOS)
Sun, 1 Nov
KSh19 839
United Airlines
UA 2296
06:20
Chicago O'Hare International Airport (ORD)
Mon, 2 Nov
2h 26min
Direct
09:46
Logan (BOS)
Mon, 2 Nov
KSh16 179
Jetblue Airways
B6 1012 🔥 Hot deal
20:15
Chicago O'Hare International Airport (ORD)
Mon, 2 Nov
2h 44min
Direct
23:59
Logan (BOS)
Mon, 2 Nov
KSh11 518
Southwest Airlines
WN 4113
08:30
Chicago Midway International Airport (MDW)
Tue, 3 Nov
2h 30min
Direct
12:00
Logan (BOS)
Tue, 3 Nov
KSh13 475
Jetblue Airways
B6 112 Best price
13:00
Chicago O'Hare International Airport (ORD)
Wed, 4 Nov
2h 48min
Direct
16:48
Logan (BOS)
Wed, 4 Nov
KSh11 218
Jetblue Airways
B6 112
13:00
Chicago O'Hare International Airport (ORD)
Thu, 12 Nov
2h 49min
Direct
16:49
Logan (BOS)
Thu, 12 Nov
KSh12 325
Southwest Airlines
WN 4113
07:40
Chicago Midway International Airport (MDW)
Sat, 14 Nov
2h 15min
Direct
10:55
Logan (BOS)
Sat, 14 Nov
KSh12 325
Jetblue Airways
B6 112
13:00
Chicago O'Hare International Airport (ORD)
Sat, 14 Nov
2h 49min
Direct
16:49
Logan (BOS)
Sat, 14 Nov
KSh13 061
American Airlines
AA 1457
20:00
Chicago O'Hare International Airport (ORD)
Sun, 15 Nov
2h 31min
Direct
23:31
Logan (BOS)
Sun, 15 Nov
KSh21 044
American Airlines
AA 1457 🔥 Hot deal
19:59
Chicago O'Hare International Airport (ORD)
Wed, 18 Nov
2h 28min
Direct
23:27
Logan (BOS)
Wed, 18 Nov
KSh11 448
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
KSh15 143
Jetblue Airways
B6 1012
02:30
Chicago O'Hare International Airport (ORD)
Sun, 22 Nov
2h 29min
Direct
05:59
Logan (BOS)
Sun, 22 Nov
KSh18 105
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
KSh17 206
Southwest Airlines
WN 2902
03:45
Chicago Midway International Airport (MDW)
Tue, 24 Nov
2h 15min
Direct
07:00
Logan (BOS)
Tue, 24 Nov
KSh14 819
Southwest Airlines
WN 4113
07:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
2h 20min
Direct
11:05
Logan (BOS)
Thu, 26 Nov
KSh19 523
United Airlines
UA 1117
18:13
Chicago O'Hare International Airport (ORD)
Thu, 26 Nov
2h 33min
Direct
21:46
Logan (BOS)
Thu, 26 Nov
KSh18 221
United Airlines
UA 2331
03:08
Chicago O'Hare International Airport (ORD)
Sat, 28 Nov
2h 33min
Direct
06:41
Logan (BOS)
Sat, 28 Nov
KSh18 221
American Airlines
AA 1515
06:00
Chicago O'Hare International Airport (ORD)
Sat, 28 Nov
2h 24min
Direct
09:24
Logan (BOS)
Sat, 28 Nov
KSh22 950
Southwest Airlines
WN 3014
05:35
Chicago Midway International Airport (MDW)
Sun, 29 Nov
2h 15min
Direct
08:50
Logan (BOS)
Sun, 29 Nov
KSh41 888
United Airlines
UA 1186
06:15
Chicago O'Hare International Airport (ORD)
Sun, 29 Nov
2h 19min
Direct
09:34
Logan (BOS)
Sun, 29 Nov
KSh40 632
Southwest Airlines
WN 4113
16:50
Chicago Midway International Airport (MDW)
Fri, 11 Dec
2h 20min
Direct
20:10
Logan (BOS)
Fri, 11 Dec
KSh16 032
Southwest Airlines
WN 4113
17:30
Chicago Midway International Airport (MDW)
Mon, 14 Dec
2h 30min
Direct
21:00
Logan (BOS)
Mon, 14 Dec
KSh14 368
Jetblue Airways
B6 1012
04:55
Chicago O'Hare International Airport (ORD)
Sat, 19 Dec
2h 26min
Direct
08:21
Logan (BOS)
Sat, 19 Dec
KSh19 754
United Airlines
UA 1707
06:20
Chicago O'Hare International Airport (ORD)
Sun, 20 Dec
2h 35min
Direct
09:55
Logan (BOS)
Sun, 20 Dec
KSh16 106
Southwest Airlines
WN 2901
01:05
Chicago Midway International Airport (MDW)
Tue, 22 Dec
2h 15min
Direct
04:20
Logan (BOS)
Tue, 22 Dec
KSh15 802
United Airlines
UA 2213
15:50
Chicago O'Hare International Airport (ORD)
Wed, 23 Dec
2h 27min
Direct
19:17
Logan (BOS)
Wed, 23 Dec
KSh14 084
American Airlines
AA 4572
00:55
Chicago O'Hare International Airport (ORD)
Thu, 24 Dec
2h 40min
Direct
04:35
Logan (BOS)
Thu, 24 Dec
KSh18 602
American Airlines
AA 1457
18:00
Chicago O'Hare International Airport (ORD)
Thu, 24 Dec
2h 51min
Direct
21:51
Logan (BOS)
Thu, 24 Dec
KSh15 166
United Airlines
UA 2213
15:50
Chicago O'Hare International Airport (ORD)
Wed, 30 Dec
2h 27min
Direct
19:17
Logan (BOS)
Wed, 30 Dec
KSh15 273
Southwest Airlines
WN 4113
16:50
Chicago Midway International Airport (MDW)
Mon, 4 Jan
2h 20min
Direct
20:10
Logan (BOS)
Mon, 4 Jan
KSh19 682
Southwest Airlines
WN 4113
17:30
Chicago Midway International Airport (MDW)
Tue, 5 Jan
2h 30min
Direct
21:00
Logan (BOS)
Tue, 5 Jan
KSh18 503
Jetblue Airways
B6 312
11:00
Chicago O'Hare International Airport (ORD)
Wed, 24 Mar
2h 24min
Direct
14:24
Logan (BOS)
Wed, 24 Mar
KSh22 353
Jetblue Airways
B6 312
19:00
Chicago O'Hare International Airport (ORD)
Mon, 19 Apr
2h 24min
Direct
22:24
Logan (BOS)
Mon, 19 Apr
KSh21 544
Jetblue Airways
B6 312
19:00
Chicago O'Hare International Airport (ORD)
Tue, 20 Apr
2h 24min
Direct
22:24
Logan (BOS)
Tue, 20 Apr
KSh21 544
United Airlines
UA 2331
02:00
Chicago O'Hare International Airport (ORD)
Wed, 5 May
2h 33min
Direct
05:33
Logan (BOS)
Wed, 5 May
KSh19 193
United Airlines
UA 2394
14:00
Chicago O'Hare International Airport (ORD)
Sun, 23 May
2h 24min
Direct
17:24
Logan (BOS)
Sun, 23 May
KSh19 245
American Airlines
AA 2784
20:59
Chicago O'Hare International Airport (ORD)
Sun, 6 June
2h 29min
Direct
00:28
Logan (BOS)
Mon, 7 June +1
KSh20 421

Direct flight schedule Chicago — Boston

Direct flights: 9 · Airlines: 4 · First departure: 02:00 · Last departure: 19:00

Departure → arrivalFlightAirport DaysDurationPrice
02:00→05:33 United Airlines UA 2331 Chicago O'HareORD MonTueWedThuFriSatSun 2h 33min
04:24→08:08 Jetblue Airways B6 1012 Chicago O'HareORD MonTueWedThuFriSatSun 2h 44min
05:20→08:46 United Airlines UA 2296 Chicago O'HareORD MonTueWedThuFriSatSun 2h 26min
06:15→09:34 United Airlines UA 1186 Chicago O'HareORD MonTueWedThuFriSatSun 2h 19min
13:00→16:49 Jetblue Airways B6 112 Chicago O'HareORD MonTueWedThuFriSatSun 2h 49min
15:50→19:17 United Airlines UA 2213 Chicago 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 Chicago O'HareORD MonTueWedThuFriSatSun 2h 28min
19:00→22:24 Jetblue Airways B6 312 Chicago 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 Tue, 27 Oct · One way from KSh13 897

Prices as of 20 October, 11:11 Moscow time

Cheap flights Chicago to Boston

Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
KSh11 218
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
KSh12 325
Allegiant Air
Allegiant Air
Fri
Price from
KSh19 328
American Airlines
American Airlines
Wed, Thu, Sat, Sun
Price from
KSh19 508
United Airlines
United Airlines
Mon, Tue, Wed, Thu, Sat, Sun
Price from
KSh40 632

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 KSh16 679.

  • Frontier Airlines Average price: KSh16 679 · Flights: 2 · Direct: 0
  • Jetblue Airways Average price: KSh16 960 · Flights: 4 · Direct: 3
  • Southwest Airlines Average price: KSh18 510 · Flights: 7 · Direct: 7
  • American Airlines Average price: KSh18 865 · Flights: 7 · Direct: 7
  • Allegiant Air Average price: KSh19 328 · Flights: 1 · Direct: 0
  • United Airlines Average price: KSh19 418 · Flights: 7 · Direct: 7

Which airlines fly most often from Chicago to Boston?

The most flight options on this route are offered by Southwest Airlines — options found: 7.

  • Southwest Airlines Flights: 7 · Direct: 7
  • American Airlines Flights: 7 · Direct: 7
  • United Airlines Flights: 7 · Direct: 7
  • Jetblue Airways Flights: 4 · Direct: 3
  • Frontier Airlines Flights: 2 · Direct: 0
  • Allegiant Air Flights: 1 · Direct: 0

Round trip Chicago — Boston

TripOutboundReturnOutbound + returnTotal
Weekend tripFri, 30 OctMon, 2 Nov KSh19 328 + KSh11 249
One weekTue, 3 NovMon, 9 Nov KSh11 518 + KSh11 218
Two weeksThu, 12 NovThu, 26 Nov KSh12 325 + KSh12 496

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 Chicago — Boston ticket?

The cheapest departure right now is Wed, 4 Nov — from KSh11 218. Days before departure: 13. 4–7 days before departure tickets cost from KSh13 897, 1–3 days before — from KSh15 621.

Before departureDeparture dateDifference from lowestPrice
1–3 days Fri, 23 Oct 39% more
4–7 days Tue, 27 Oct 24% more
8–14 days Wed, 4 Nov cheapest
15–21 days Thu, 12 Nov 10% more
22–30 days Thu, 19 Nov 2% more

Lowest prices for departures in the next 30 days.

How many flights per day operate from Chicago to Boston?

Most flights operate on Wed (11), the fewest on Fri (4).

  • Mon Flights: 6 · Direct: 5
  • Tue Flights: 8 · Direct: 8
  • Wed Flights: 11 · Direct: 9
  • Thu Flights: 6 · Direct: 6
  • Fri Flights: 4 · Direct: 3
  • Sat Flights: 6 · Direct: 5
  • Sun Flights: 9 · Direct: 9

Popular destinations from Chicago

All →
CHI
Chicago — Nashville
United States → United States
BNA
from
KSh3 500
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
KSh3 978
CHI
Chicago — Baltimore
United States → United States
BWI
from
KSh4 310
CHI
Chicago — Washington
United States → United States
WAS
from
KSh5 691
CHI
Chicago — Burlington
United States → United States
BRL
from
KSh6 404
CHI
Chicago — Denver
United States → United States
DEN
from
KSh6 538
CHI
Chicago — Miami
United States → United States
MIA
from
KSh6 773
CHI
Chicago — Phoenix
United States → United States
PHX
from
KSh6 933

Popular destinations to Boston

All →
WAS
Washington — Boston
United States → United States
BOS
from
KSh7 429
ATL
Atlanta — Boston
United States → United States
BOS
from
KSh11 310
ORL
Orlando — Boston
United States → United States
BOS
from
KSh11 831
PHL
Philadelphia — Boston
United States → United States
BOS
from
KSh12 170
DEN
Denver — Boston
United States → United States
BOS
from
KSh12 574
FLL
Fort Lauderdale — Boston
United States → United States
BOS
from
KSh13 870
NYC
New York — Boston
United States → United States
BOS
from
KSh15 392
YTO
Toronto — Boston
Canada → United States
BOS
from
KSh15 424

Flights from Chicago to cities near Boston

Flights to Boston are currently cheaper than to nearby cities: from KSh11 218.

City Distance Direct Flights Airlines Price from
BostonBOS — 24266
ProvidencePVD 78 km 244
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
KSh11 218
Average price
KSh18 221
Flight time
2 hours 28 minutes
Distance
1 389 km
Рейсов в неделю
44
Airlines
6
Most frequent flight
WN 4113

Prices as of 20 October, 11:10 Moscow time

Airports on the Chicago — Boston route

From → to Flights Direct Airlines Price from
Chicago O'Hare International AirportORD LoganBOS Cheapest
17173
Chicago Midway International AirportMDW LoganBOS
973

Departure airports · Chicago

Arrival airports · Boston

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

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3 GB

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30

days

KSh1 133

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2 GB

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15

days

KSh1 574

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5 GB

data

30

days

KSh1 763

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data

30

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KSh2 015

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30

days

KSh2 833

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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 28 minutes on average. Nonstop tickets start at KSh11 218.
The average ticket price Chicago Boston is KSh18 221. The cheapest ticket costs KSh11 218, operated by Jetblue Airways, flight B6 112, departing Chicago on 4 November at 13:00, arriving Boston on 4 November at 16:48. Prices as of 20 October.
A nonstop flight takes 2 hours 28 minutes on average. The fastest is WN 4113 Southwest Airlines: 2 hours 15 minutes. With a connection: from 12 hours 29 minutes.
Flights from Chicago to Boston depart from these airports: Chicago O'Hare International Airport (ORD), Chicago Midway International Airport (MDW). Most flights depart from Chicago O'Hare International Airport. Arrival: Logan (BOS).
Based on prices for the coming months, the cheapest month to fly is November: tickets from KSh11 218. The most expensive month is December, with tickets from KSh14 368.
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 KSh10 789. The average price is KSh16 975. Nonstop flights are operated by: American Airlines, Southwest Airlines, Jetblue Airways, United Airlines. All tickets Boston — Chicago