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Cheap flights Boston (Logan) to Chicago Midway International Airport

1 passenger, economy

Nonstop flights from Boston to Chicago Midway International Airport: Southwest Airlines. Nonstop flights per week: 32. Flight time: 2 hours 45 minutes. Distance: 1379 km. Tickets from A$130 (departure 20 November).

Prices updated on 24 October at 11:04

See also: Flights from Boston (Logan)Flights to Chicago Midway International Airport (Chicago)

Cheap flights Boston to Chicago Midway International Airport

Compare prices, duration and stops

Southwest Airlines
WN 1346
09:40
Logan (BOS)
Sat, 24 Oct
2h 35min
Direct
11:15
Chicago Midway International Airport (MDW)
Sat, 24 Oct
A$281
Southwest Airlines
WN 4568
13:10
Logan (BOS)
Sun, 25 Oct
2h 35min
Direct
14:45
Chicago Midway International Airport (MDW)
Sun, 25 Oct
A$327
Southwest Airlines
WN 805
12:50
Logan (BOS)
Mon, 26 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Mon, 26 Oct
A$166
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
A$230
Southwest Airlines
WN 805
14:20
Logan (BOS)
Tue, 27 Oct
2h 35min
Direct
15:55
Chicago Midway International Airport (MDW)
Tue, 27 Oct
A$162
Southwest Airlines
WN 2046
17:55
Logan (BOS)
Tue, 27 Oct
2h 35min
Direct
19:30
Chicago Midway International Airport (MDW)
Tue, 27 Oct
A$147
Frontier Airlines
F9 3511
11:12
Logan (BOS)
Tue, 27 Oct
7h 15min
1 stop
17:27
Chicago Midway International Airport (MDW)
Tue, 27 Oct
A$222
Southwest Airlines
WN 2046
17:55
Logan (BOS)
Wed, 28 Oct
2h 35min
Direct
19:30
Chicago Midway International Airport (MDW)
Wed, 28 Oct
A$146
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Wed, 28 Oct
12h 8min
1 stop
23:47
Chicago Midway International Airport (MDW)
Wed, 28 Oct
A$213
Southwest Airlines
WN 807
12:50
Logan (BOS)
Wed, 28 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Wed, 28 Oct
A$223
Southwest Airlines
WN 805
12:50
Logan (BOS)
Thu, 29 Oct
2h 35min
Direct
14:25
Chicago Midway International Airport (MDW)
Thu, 29 Oct
A$166
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
A$227
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Fri, 30 Oct
12h 8min
1 stop
23:47
Chicago Midway International Airport (MDW)
Fri, 30 Oct
A$193
Frontier Airlines
F9 3511
11:27
Logan (BOS)
Sat, 31 Oct
7h 20min
1 stop
17:47
Chicago Midway International Airport (MDW)
Sat, 31 Oct
A$195
Southwest Airlines
WN 792
05:35
Logan (BOS)
Sun, 1 Nov
11h 25min
1 stop
16:00
Chicago Midway International Airport (MDW)
Sun, 1 Nov
A$278
Allegiant Air
G4 3473
12:34
Logan (BOS)
Sun, 1 Nov
45h 21min
1 stop
08:55
Chicago Midway International Airport (MDW)
Tue, 3 Nov +1
A$254
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Sun, 1 Nov
12h 8min
1 stop
23:47
Chicago Midway International Airport (MDW)
Sun, 1 Nov
A$337
Southwest Airlines
WN 816
02:30
Logan (BOS)
Mon, 2 Nov
2h 45min
Direct
04:15
Chicago Midway International Airport (MDW)
Mon, 2 Nov
A$494
Southwest Airlines
WN 819
13:10
Logan (BOS)
Mon, 2 Nov
10h
1 stop
22:10
Chicago Midway International Airport (MDW)
Mon, 2 Nov
A$197
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Mon, 2 Nov
12h 8min
1 stop
23:47
Chicago Midway International Airport (MDW)
Mon, 2 Nov
A$247
Southwest Airlines
WN 0800
22:25
Logan (BOS)
Mon, 2 Nov
6h 45min
1 stop
04:10
Chicago Midway International Airport (MDW)
Tue, 3 Nov +1
A$232
Southwest Airlines
WN 956
21:00
Logan (BOS)
Mon, 2 Nov
16h 5min
2 stops
12:05
Chicago Midway International Airport (MDW)
Tue, 3 Nov +1
A$193
Frontier Airlines
F9 3511
12:15
Logan (BOS)
Tue, 3 Nov
6h 32min
1 stop
17:47
Chicago Midway International Airport (MDW)
Tue, 3 Nov
A$196
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
A$157
Frontier Airlines
F9 3511
12:39
Logan (BOS)
Wed, 4 Nov
12h 8min
1 stop
23:47
Chicago Midway International Airport (MDW)
Wed, 4 Nov
A$203
Southwest Airlines
WN 813
12:50
Logan (BOS)
Wed, 4 Nov
2h 50min
Direct
14:40
Chicago Midway International Airport (MDW)
Wed, 4 Nov
A$154
Southwest Airlines
WN 816 🔥 Hot deal
17:55
Logan (BOS)
Wed, 4 Nov
2h 45min
Direct
19:40
Chicago Midway International Airport (MDW)
Wed, 4 Nov
A$155
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Thu, 5 Nov
12h 8min
1 stop
07:47
Chicago Midway International Airport (MDW)
Fri, 6 Nov +1
A$142
Southwest Airlines
WN 816
02:30
Logan (BOS)
Fri, 6 Nov
2h 45min
Direct
04:15
Chicago Midway International Airport (MDW)
Fri, 6 Nov
A$172
Southwest Airlines
WN 816
18:30
Logan (BOS)
Fri, 6 Nov
2h 45min
Direct
20:15
Chicago Midway International Airport (MDW)
Fri, 6 Nov
A$262
Southwest Airlines
WN 787
16:10
Logan (BOS)
Sat, 7 Nov
8h 25min
1 stop
23:35
Chicago Midway International Airport (MDW)
Sat, 7 Nov
A$188
Frontier Airlines
F9 3511
11:27
Logan (BOS)
Sat, 7 Nov
7h 20min
1 stop
17:47
Chicago Midway International Airport (MDW)
Sat, 7 Nov
A$169
Southwest Airlines
WN 2185
07:05
Logan (BOS)
Mon, 9 Nov
2h 45min
Direct
08:50
Chicago Midway International Airport (MDW)
Mon, 9 Nov
A$154
Southwest Airlines
WN 813
20:45
Logan (BOS)
Mon, 9 Nov
2h 45min
Direct
22:30
Chicago Midway International Airport (MDW)
Mon, 9 Nov
A$196
Southwest Airlines
WN 791
03:30
Logan (BOS)
Tue, 10 Nov
5h 40min
1 stop
08:10
Chicago Midway International Airport (MDW)
Tue, 10 Nov
A$163
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Fri, 13 Nov
12h 8min
1 stop
07:47
Chicago Midway International Airport (MDW)
Sat, 14 Nov +1
A$222
Southwest Airlines
WN 2758
15:10
Logan (BOS)
Sat, 14 Nov
2h 45min
Direct
16:55
Chicago Midway International Airport (MDW)
Sat, 14 Nov
A$144
Southwest Airlines
WN 819
05:10
Logan (BOS)
Sun, 15 Nov
10h
1 stop
14:10
Chicago Midway International Airport (MDW)
Sun, 15 Nov
A$228
Southwest Airlines
WN 792
05:35
Logan (BOS)
Sun, 15 Nov
9h 15min
2 stops
13:50
Chicago Midway International Airport (MDW)
Sun, 15 Nov
A$198
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
A$198
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Wed, 18 Nov
12h 8min
1 stop
07:47
Chicago Midway International Airport (MDW)
Thu, 19 Nov +1
A$207
Frontier Airlines
F9 3511
20:39
Logan (BOS)
Thu, 19 Nov
12h 8min
1 stop
07:47
Chicago Midway International Airport (MDW)
Fri, 20 Nov +1
A$207
Frontier Airlines
F9 1977 Best price
11:06
Logan (BOS)
Fri, 20 Nov
9h 41min
1 stop
19:47
Chicago Midway International Airport (MDW)
Fri, 20 Nov
A$130
Southwest Airlines
WN 481
15:45
Logan (BOS)
Thu, 26 Nov
9h 35min
1 stop
00:20
Chicago Midway International Airport (MDW)
Fri, 27 Nov +1
A$204
Southwest Airlines
WN 0813
13:05
Logan (BOS)
Thu, 26 Nov
2h 40min
Direct
14:45
Chicago Midway International Airport (MDW)
Thu, 26 Nov
A$146
Southwest Airlines
WN 2185
07:05
Logan (BOS)
Fri, 27 Nov
2h 45min
Direct
08:50
Chicago Midway International Airport (MDW)
Fri, 27 Nov
A$227
Southwest Airlines
WN 813
12:50
Logan (BOS)
Tue, 1 Dec
2h 50min
Direct
14:40
Chicago Midway International Airport (MDW)
Tue, 1 Dec
A$246
Frontier Airlines
F9 1977
11:08
Logan (BOS)
Mon, 7 Dec
10h 34min
1 stop
20:42
Chicago Midway International Airport (MDW)
Mon, 7 Dec
A$149
Southwest Airlines
WN 813
12:50
Logan (BOS)
Tue, 8 Dec
2h 50min
Direct
14:40
Chicago Midway International Airport (MDW)
Tue, 8 Dec
A$154
Frontier Airlines
F9 1977
11:08
Logan (BOS)
Thu, 10 Dec
10h 34min
1 stop
20:42
Chicago Midway International Airport (MDW)
Thu, 10 Dec
A$241

Direct flight schedule Boston — Chicago Midway International Airport

Direct flights: 9 · First departure: 06:25 · Last departure: 17:55

Departure → arrivalFlightAirport DaysDurationPrice
06:25→08:10 Southwest Airlines WN 816 LoganBOS MonTueWedThuFriSatSun 2h 45min
07:05→08:50 Southwest Airlines WN 2185 LoganBOS MonTueWedThuFriSatSun 2h 45min
07:15→09:05 Southwest Airlines WN 4127 LoganBOS MonTueWedThuFriSatSun 2h 50min
07:30→09:15 Southwest Airlines WN 4695 LoganBOS MonTueWedThuFriSatSun 2h 45min
12:50→14:25 Southwest Airlines WN 805 LoganBOS MonTueWedThuFriSatSun 2h 35min
12:50→14:35 Southwest Airlines WN 813 LoganBOS MonTueWedThuFriSatSun 2h 45min
13:10→14:55 Southwest Airlines WN 698 LoganBOS MonTueWedThuFriSatSun 2h 45min
15:10→16:55 Southwest Airlines WN 2758 LoganBOS MonTueWedThuFriSatSun 2h 45min
17:55→19:30 Southwest Airlines WN 2046 LoganBOS MonTueWedThuFriSatSun 2h 35min
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 Fri, 30 Oct · One way from A$193

Prices as of 24 October, 11:05 Moscow time

Cheap flights Boston to Chicago Midway International Airport

Frontier Airlines
Frontier Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
A$130
Southwest Airlines
Southwest Airlines
Mon, Tue, Wed, Thu, Fri, Sat, Sun
Price from
A$144

Which airlines offer the cheapest flights from Boston to Chicago Midway International Airport?

Based on collected data, the cheapest flights are offered by Frontier Airlines with an average ticket price of A$206.

  • Frontier Airlines Average price: A$206 · Flights: 2 · Direct: 0
  • Southwest Airlines Average price: A$218 · Flights: 27 · Direct: 16
  • Allegiant Air Average price: A$254 · Flights: 1 · Direct: 0
  • Jetblue Airways Average price: A$2 377 · Flights: 1 · Direct: 0

Which airlines fly most often from Boston to Chicago Midway International Airport?

The most flight options on this route are offered by Southwest Airlines — options found: 27.

  • Southwest Airlines Flights: 27 · Direct: 16
  • Frontier Airlines Flights: 2 · Direct: 0
  • Allegiant Air Flights: 1 · Direct: 0
  • Jetblue Airways Flights: 1 · Direct: 0

Round trip Boston — Chicago Midway International Airport

TripOutboundReturnOutbound + returnTotal
Weekend tripSat, 12 DecMon, 14 Dec A$154 + A$168
One weekWed, 4 NovThu, 12 Nov A$131 + A$144
Two weeksWed, 4 NovThu, 19 Nov A$131 + A$134

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

Prices as of 24 October, 11:05 Moscow time

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

The cheapest departure right now is Fri, 20 Nov — from A$130. Days before departure: 27. 4–7 days before departure tickets cost from A$193, 1–3 days before — from A$222.

Before departureDeparture dateDifference from lowestPrice
1–3 days Tue, 27 Oct 70% more
4–7 days Fri, 30 Oct 48% more
8–14 days Thu, 5 Nov 9% more
15–21 days Sat, 14 Nov 11% more
22–30 days Fri, 20 Nov cheapest

Lowest prices for departures in the next 30 days.

How many flights per day operate from Boston to Chicago Midway International Airport?

Most flights operate on Mon (12), the fewest on Wed (6).

  • Mon Flights: 12 · Direct: 7
  • Tue Flights: 9 · Direct: 5
  • Wed Flights: 6 · Direct: 5
  • Thu Flights: 9 · Direct: 5
  • Fri Flights: 8 · Direct: 5
  • Sat Flights: 7 · Direct: 3
  • Sun Flights: 6 · Direct: 2

Popular destinations from Boston

All →
BOS
Boston — Lebanon
United States → United States
LEB
from
A$98
BOS
Boston — Rutland
United States → United States
RUT
from
A$111
BOS
Boston — Washington
United States → United States
WAS
from
A$114
BOS
Boston — Chicago
United States → United States
CHI
from
A$130
BOS
Boston — Orlando
United States → United States
ORL
from
A$133
BOS
Boston — Philadelphia
United States → United States
PHL
from
A$134

Popular destinations to Chicago Midway International Airport

All →
ATL
Atlanta — Chicago
United States → United States
MDW
from
A$64
FLL
Fort Lauderdale — Chicago
United States → United States
MDW
from
A$76
DFW
Dallas — Chicago
United States → United States
MDW
from
A$77
PHL
Philadelphia — Chicago
United States → United States
MDW
from
A$114
DEN
Denver — Chicago
United States → United States
MDW
from
A$119
BNA
Nashville — Chicago
United States → United States
MDW
from
A$137
NYC
New York — Chicago
United States → United States
MDW
from
A$137
LAX
Los Angeles — Chicago
United States → United States
MDW
from
A$142

Cheap flights Boston to Chicago Midway International Airport

Price from
A$130
Average price
A$210
Flight time
2 hours 45 minutes
Distance
1 379 km
Рейсов в неделю
32
Airlines
4
Most frequent flight
WN 816

Prices as of 24 October, 11:04 Moscow time

Airports on the Boston — Chicago Midway International Airport route

From → to Flights Direct Airlines Price from
LoganBOS Chicago Midway International AirportMDW
31164

Departure airports · Boston

Arrival airports · Chicago Midway International Airport

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

All plans

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30

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A$13

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2 GB

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15

days

A$18

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5 GB

data

30

days

A$20

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3 GB

data

30

days

A$23

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30

days

A$32

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Frequently Asked Questions

Yes. Nonstop flights from Boston to Chicago Midway International Airport are operated by: Southwest Airlines. A nonstop flight takes 2 hours 45 minutes on average. Nonstop tickets start at A$144.
The average ticket price Boston Chicago Midway International Airport is A$210. The cheapest ticket costs A$130, operated by Frontier Airlines, flight F9 1977, departing Boston on 20 November at 11:06, arriving Chicago Midway International Airport on 20 November at 19:47. Prices as of 24 October.
A nonstop flight takes 2 hours 45 minutes on average. The fastest is WN 2046 Southwest Airlines: 2 hours 35 minutes. With a connection: from 4 hours 30 minutes, usually about 10 hours.
Based on prices for the coming months, the cheapest month to fly is November: tickets from A$130. The most expensive month is October, with tickets from A$193.
Tickets from Boston to Chicago Midway International Airport are sold by: Southwest Airlines, Frontier Airlines, Jetblue Airways, Allegiant Air. Nonstop: Southwest Airlines.
The distance from Boston to Chicago Midway International Airport is 1379 km.
The first nonstop flight departs at 06:25 (WN 816, Southwest Airlines), the last one at 17:55 (WN 2046, Southwest Airlines). Local time.
Yes, the time difference is 1 hour: Boston — UTC−4, Chicago Midway International Airport — UTC−5. For example: Boston 12:00 → Chicago Midway International Airport 11:00.