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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: 41. Flight time: 2 hours 29 minutes. Distance: 1389 km. Tickets from C$128 (departure 4 November).

Prices updated on 29 October at 11:04

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

Cheap flights Chicago to Boston

Compare prices, duration and stops

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
C$221
Southwest Airlines
WN 2213
15:30
Chicago Midway International Airport (MDW)
Fri, 30 Oct
2h 20min
Direct
18:50
Logan (BOS)
Fri, 30 Oct
C$237
Southwest Airlines
WN 4113
07:50
Chicago Midway International Airport (MDW)
Sun, 1 Nov
2h 20min
Direct
11:10
Logan (BOS)
Sun, 1 Nov
C$237
American Airlines
AA 469
17:52
O'Hare International Airport (ORD)
Sun, 1 Nov
2h 34min
Direct
21:26
Logan (BOS)
Sun, 1 Nov
C$220
Jetblue Airways
B6 1012
20:15
O'Hare International Airport (ORD)
Sun, 1 Nov
2h 44min
Direct
23:59
Logan (BOS)
Sun, 1 Nov
C$227
United Airlines
UA 2296
06:20
O'Hare International Airport (ORD)
Mon, 2 Nov
2h 26min
Direct
09:46
Logan (BOS)
Mon, 2 Nov
C$185
Southwest Airlines
WN 2902
18:45
Chicago Midway International Airport (MDW)
Mon, 2 Nov
2h 15min
Direct
22:00
Logan (BOS)
Mon, 2 Nov
C$251
Jetblue Airways
B6 1012 🔥 Hot deal
20:15
O'Hare International Airport (ORD)
Mon, 2 Nov
2h 44min
Direct
23:59
Logan (BOS)
Mon, 2 Nov
C$132
Southwest Airlines
WN 4113
08:30
Chicago Midway International Airport (MDW)
Tue, 3 Nov
2h 30min
Direct
12:00
Logan (BOS)
Tue, 3 Nov
C$154
American Airlines
AA 1951
06:00
O'Hare International Airport (ORD)
Wed, 4 Nov
2h 29min
Direct
09:29
Logan (BOS)
Wed, 4 Nov
C$210
Jetblue Airways
B6 112 Best price
13:00
O'Hare International Airport (ORD)
Wed, 4 Nov
2h 48min
Direct
16:48
Logan (BOS)
Wed, 4 Nov
C$128
American Airlines
AA 1457
19:59
O'Hare International Airport (ORD)
Wed, 4 Nov
2h 28min
Direct
23:27
Logan (BOS)
Wed, 4 Nov
C$239
American Airlines
AA 1457
20:00
O'Hare International Airport (ORD)
Fri, 6 Nov
2h 31min
Direct
23:31
Logan (BOS)
Fri, 6 Nov
C$217
Jetblue Airways
B6 112
13:00
O'Hare International Airport (ORD)
Thu, 12 Nov
2h 49min
Direct
16:49
Logan (BOS)
Thu, 12 Nov
C$141
Southwest Airlines
WN 4113
07:40
Chicago Midway International Airport (MDW)
Sat, 14 Nov
2h 15min
Direct
10:55
Logan (BOS)
Sat, 14 Nov
C$141
Jetblue Airways
B6 112
13:00
O'Hare International Airport (ORD)
Sat, 14 Nov
2h 49min
Direct
16:49
Logan (BOS)
Sat, 14 Nov
C$216
American Airlines
AA 1457
20:00
O'Hare International Airport (ORD)
Sun, 15 Nov
2h 31min
Direct
23:31
Logan (BOS)
Sun, 15 Nov
C$240
American Airlines
AA 1457 🔥 Hot deal
19:59
O'Hare International Airport (ORD)
Wed, 18 Nov
2h 28min
Direct
23:27
Logan (BOS)
Wed, 18 Nov
C$131
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
C$173
Jetblue Airways
B6 1012
02:30
O'Hare International Airport (ORD)
Sun, 22 Nov
2h 29min
Direct
05:59
Logan (BOS)
Sun, 22 Nov
C$207
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
C$151
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
C$197
Southwest Airlines
WN 2902
03:45
Chicago Midway International Airport (MDW)
Tue, 24 Nov
2h 15min
Direct
07:00
Logan (BOS)
Tue, 24 Nov
C$169
Southwest Airlines
WN 4113
07:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
2h 20min
Direct
11:05
Logan (BOS)
Thu, 26 Nov
C$223
United Airlines
UA 1117
18:13
O'Hare International Airport (ORD)
Thu, 26 Nov
2h 33min
Direct
21:46
Logan (BOS)
Thu, 26 Nov
C$208
United Airlines
UA 2331
03:08
O'Hare International Airport (ORD)
Sat, 28 Nov
2h 33min
Direct
06:41
Logan (BOS)
Sat, 28 Nov
C$208
American Airlines
AA 1515
06:00
O'Hare International Airport (ORD)
Sat, 28 Nov
2h 24min
Direct
09:24
Logan (BOS)
Sat, 28 Nov
C$262
Southwest Airlines
WN 3014
05:35
Chicago Midway International Airport (MDW)
Sun, 29 Nov
2h 15min
Direct
08:50
Logan (BOS)
Sun, 29 Nov
C$479
United Airlines
UA 1186
06:15
O'Hare International Airport (ORD)
Sun, 29 Nov
2h 19min
Direct
09:34
Logan (BOS)
Sun, 29 Nov
C$464
Southwest Airlines
WN 4113
16:50
Chicago Midway International Airport (MDW)
Fri, 11 Dec
2h 20min
Direct
20:10
Logan (BOS)
Fri, 11 Dec
C$183
Southwest Airlines
WN 4113
17:30
Chicago Midway International Airport (MDW)
Mon, 14 Dec
2h 30min
Direct
21:00
Logan (BOS)
Mon, 14 Dec
C$164
Jetblue Airways
B6 1012
04:55
O'Hare International Airport (ORD)
Sat, 19 Dec
2h 26min
Direct
08:21
Logan (BOS)
Sat, 19 Dec
C$226
United Airlines
UA 1707
06:20
O'Hare International Airport (ORD)
Sun, 20 Dec
2h 35min
Direct
09:55
Logan (BOS)
Sun, 20 Dec
C$184
Southwest Airlines
WN 2901
01:05
Chicago Midway International Airport (MDW)
Tue, 22 Dec
2h 15min
Direct
04:20
Logan (BOS)
Tue, 22 Dec
C$181
United Airlines
UA 2213
15:50
O'Hare International Airport (ORD)
Wed, 23 Dec
2h 27min
Direct
19:17
Logan (BOS)
Wed, 23 Dec
C$161
American Airlines
AA 4572
00:55
O'Hare International Airport (ORD)
Thu, 24 Dec
2h 40min
Direct
04:35
Logan (BOS)
Thu, 24 Dec
C$213
American Airlines
AA 1457
18:00
O'Hare International Airport (ORD)
Thu, 24 Dec
2h 51min
Direct
21:51
Logan (BOS)
Thu, 24 Dec
C$173
Southwest Airlines
WN 2902
18:25
Chicago Midway International Airport (MDW)
Fri, 25 Dec
2h 20min
Direct
21:45
Logan (BOS)
Fri, 25 Dec
C$154
United Airlines
UA 2213
15:50
O'Hare International Airport (ORD)
Wed, 30 Dec
2h 27min
Direct
19:17
Logan (BOS)
Wed, 30 Dec
C$175
Southwest Airlines
WN 4113
16:50
Chicago Midway International Airport (MDW)
Mon, 4 Jan
2h 20min
Direct
20:10
Logan (BOS)
Mon, 4 Jan
C$225
Southwest Airlines
WN 4113
17:30
Chicago Midway International Airport (MDW)
Tue, 5 Jan
2h 30min
Direct
21:00
Logan (BOS)
Tue, 5 Jan
C$211
Jetblue Airways
B6 312
11:00
O'Hare International Airport (ORD)
Wed, 24 Mar
2h 24min
Direct
14:24
Logan (BOS)
Wed, 24 Mar
C$255
Jetblue Airways
B6 312
14:30
O'Hare International Airport (ORD)
Wed, 24 Mar
2h 31min
Direct
18:01
Logan (BOS)
Wed, 24 Mar
C$256
American Airlines
AA 1073
17:21
O'Hare International Airport (ORD)
Wed, 24 Mar
2h 31min
Direct
20:52
Logan (BOS)
Wed, 24 Mar
C$266
Jetblue Airways
B6 312
19:00
O'Hare International Airport (ORD)
Mon, 19 Apr
2h 24min
Direct
22:24
Logan (BOS)
Mon, 19 Apr
C$246
Jetblue Airways
B6 312
19:00
O'Hare International Airport (ORD)
Tue, 20 Apr
2h 24min
Direct
22:24
Logan (BOS)
Tue, 20 Apr
C$246
United Airlines
UA 2331
02:00
O'Hare International Airport (ORD)
Wed, 5 May
2h 33min
Direct
05:33
Logan (BOS)
Wed, 5 May
C$219
United Airlines
UA 2394
14:00
O'Hare International Airport (ORD)
Sun, 23 May
2h 24min
Direct
17:24
Logan (BOS)
Sun, 23 May
C$220
American Airlines
AA 2784
20:59
O'Hare International Airport (ORD)
Sun, 6 June
2h 29min
Direct
00:28
Logan (BOS)
Mon, 7 June +1
C$233
American Airlines
AA 3107
19:29
O'Hare International Airport (ORD)
Mon, 19 July
2h 37min
Direct
23:06
Logan (BOS)
Mon, 19 July
C$236

Direct flight schedule Chicago — Boston

Direct flights: 8 · Airlines: 4 · First departure: 02:00 · Last departure: 20:15

Departure → arrivalFlightAirport DaysDurationPrice
02:00→05:33 United Airlines UA 2331 O'HareORD MonTueWedThuFriSatSun 2h 33min
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
19:00→22:24 Jetblue Airways B6 312 O'HareORD MonTueWedThuFriSatSun 2h 24min
19:59→23:27 American Airlines AA 1457 O'HareORD MonTueWedThuFriSatSun 2h 28min
20:15→23:59 Jetblue Airways B6 1012 O'HareORD MonTueWedThuFriSatSun 2h 44min
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, 29 Oct · One way from C$202

Prices as of 29 October, 11:05 Moscow time

Cheap flights Chicago to Boston

Frontier Airlines
Frontier Airlines
Mon, Sat
Price from
C$151
Southwest Airlines
Southwest Airlines
Mon, Tue, Thu, Fri, Sat, Sun
Price from
C$154
American Airlines
American Airlines
Mon, Wed, Thu, Fri, Sat, Sun
Price from
C$210
Jetblue Airways
Jetblue Airways
Mon, Tue, Wed, Thu, Sat, Sun
Price from
C$216
United Airlines
United Airlines
Mon, Wed, Thu, Sat, Sun
Price from
C$464

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 C$174.

  • Frontier Airlines Average price: C$174 · Flights: 1 · Direct: 0
  • Jetblue Airways Average price: C$207 · Flights: 3 · Direct: 3
  • Southwest Airlines Average price: C$215 · Flights: 5 · Direct: 5
  • Allegiant Air Average price: C$221 · Flights: 1 · Direct: 0
  • American Airlines Average price: C$223 · Flights: 9 · Direct: 9
  • United Airlines Average price: C$225 · Flights: 7 · Direct: 7

Which airlines fly most often from Chicago to Boston?

The most flight options on this route are offered by American Airlines — options found: 9.

  • American Airlines Flights: 9 · Direct: 9
  • United Airlines Flights: 7 · Direct: 7
  • Southwest Airlines Flights: 5 · Direct: 5
  • Jetblue Airways Flights: 3 · Direct: 3
  • Frontier Airlines Flights: 1 · Direct: 0
  • Allegiant Air Flights: 1 · Direct: 0

Round trip Chicago — Boston

TripOutboundReturnOutbound + returnTotal
Weekend tripSat, 7 NovMon, 9 Nov C$217 + C$128
One weekThu, 12 NovFri, 20 Nov C$141 + C$127
Two weeksThu, 12 NovThu, 26 Nov C$141 + C$143

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

Prices as of 29 October, 11:05 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 C$131. Days before departure: 21. 4–7 days before departure tickets cost from C$210, 1–3 days before — from C$220.

Before departureDeparture dateDifference from lowestPrice
1–3 days Sun, 1 Nov 68% more
4–7 days Wed, 4 Nov 61% more
8–14 days Thu, 12 Nov 8% more
15–21 days Thu, 19 Nov cheapest
22–30 days Sun, 22 Nov 15% 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 (9), the fewest on Tue (4).

  • Mon Flights: 7 · Direct: 6
  • Tue Flights: 4 · Direct: 4
  • Wed Flights: 8 · Direct: 8
  • Thu Flights: 5 · Direct: 5
  • Fri Flights: 5 · Direct: 4
  • Sat Flights: 6 · Direct: 5
  • Sun Flights: 9 · Direct: 9

Popular destinations from Chicago

All →
CHI
Chicago — Fort Lauderdale
United States → United States
FLL
from
C$43
CHI
Chicago — Denver
United States → United States
DEN
from
C$44
CHI
Chicago — Baltimore
United States → United States
BWI
from
C$46
CHI
Chicago — Washington
United States → United States
WAS
from
C$64
CHI
Chicago — Miami
United States → United States
MIA
from
C$71
CHI
Chicago — St Louis
United States → United States
STL
from
C$77
CHI
Chicago — Atlanta
United States → United States
ATL
from
C$77
CHI
Chicago — Memphis
United States → United States
MEM
from
C$81
CHI
Chicago — Tampa
United States → United States
TPA
from
C$81

Popular destinations to Boston

All →
FLL
Fort Lauderdale — Boston
United States → United States
BOS
from
C$78
PHL
Philadelphia — Boston
United States → United States
BOS
from
C$106
DEN
Denver — Boston
United States → United States
BOS
from
C$144
LAS
Las Vegas — Boston
United States → United States
BOS
from
C$154
PHX
Phoenix — Boston
United States → United States
BOS
from
C$155
SFO
San Francisco — Boston
United States → United States
BOS
from
C$165
NYC
New York — Boston
United States → United States
BOS
from
C$176
LAX
Los Angeles — Boston
United States → United States
BOS
from
C$188

Flights from Chicago to cities near Boston

Flights to Boston are currently cheaper than to nearby cities: from C$128.

City Distance Direct Flights Airlines Price from
BostonBOS — 24266
ProvidencePVD 78 km 022
PortlandPWM 153 km 122

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

Cheap flights Chicago to Boston

Price from
C$131
Average price
C$216
Flight time
2 hours 29 minutes
Distance
1 389 km
Рейсов в неделю
41
Airlines
6
Most frequent flight
AA 1457

Prices as of 29 October, 11:04 Moscow time

Airports on the Chicago — Boston route

From → to Flights Direct Airlines Price from
O'Hare International AirportORD LoganBOS Cheapest
19193
Chicago Midway International AirportMDW LoganBOS
753

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 C$128.
The average ticket price Chicago Boston is C$216. The cheapest ticket costs C$128, 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 29 October.
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 12 hours 29 minutes.
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 C$131. The most expensive month is December, with tickets from C$154.
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 C$123. The average price is C$191. Nonstop flights are operated by: American Airlines, Southwest Airlines, Jetblue Airways, United Airlines. All tickets Boston — Chicago