Cheap flights Boston (Logan) to Chicago Midway International Airport

From

To

Depart

Return

Passengers

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 81 € (departure 20 November).

Prices updated on 25 October at 11:06

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

Filters

Stops

Direct only 1 stop 2+ stops

Price

81 € 1 486 € 1 486 €

Airlines

Allegiant Air Frontier Airlines Jetblue Airways Southwest Airlines

WN 4568

13:10

Logan (BOS)

Sun, 25 Oct

2h 35min

Direct

14:45

Chicago Midway International Airport (MDW)

Sun, 25 Oct

204 €

WN 1383

22:50

Logan (BOS)

Sun, 25 Oct

2h 40min

Direct

00:30

Chicago Midway International Airport (MDW)

Mon, 26 Oct +1

210 €

WN 805

12:50

Logan (BOS)

Mon, 26 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Mon, 26 Oct

104 €

F9 3511

12:57

Logan (BOS)

Mon, 26 Oct

11h 46min

1 stop

23:43

Chicago Midway International Airport (MDW)

Mon, 26 Oct

144 €

WN 805

14:20

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

15:55

Chicago Midway International Airport (MDW)

Tue, 27 Oct

102 €

WN 2046

17:55

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Tue, 27 Oct

92 €

F9 3511

11:12

Logan (BOS)

Tue, 27 Oct

7h 15min

1 stop

17:27

Chicago Midway International Airport (MDW)

Tue, 27 Oct

139 €

WN 2046

17:55

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Wed, 28 Oct

92 €

F9 3511

12:39

Logan (BOS)

Wed, 28 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 28 Oct

133 €

WN 807

12:50

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Wed, 28 Oct

139 €

WN 805

12:50

Logan (BOS)

Thu, 29 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Thu, 29 Oct

104 €

F9 3511

12:39

Logan (BOS)

Thu, 29 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Thu, 29 Oct

142 €

F9 3511

12:39

Logan (BOS)

Fri, 30 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Fri, 30 Oct

121 €

F9 3511

11:27

Logan (BOS)

Sat, 31 Oct

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 31 Oct

122 €

WN 792

05:35

Logan (BOS)

Sun, 1 Nov

11h 25min

1 stop

16:00

Chicago Midway International Airport (MDW)

Sun, 1 Nov

174 €

G4 3473

12:34

Logan (BOS)

Sun, 1 Nov

45h 21min

1 stop

08:55

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

159 €

F9 3511

12:39

Logan (BOS)

Sun, 1 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Sun, 1 Nov

211 €

WN 816

02:30

Logan (BOS)

Mon, 2 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Mon, 2 Nov

309 €

WN 819

13:10

Logan (BOS)

Mon, 2 Nov

10h

1 stop

22:10

Chicago Midway International Airport (MDW)

Mon, 2 Nov

123 €

F9 3511

12:39

Logan (BOS)

Mon, 2 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Mon, 2 Nov

154 €

WN 0800

22:25

Logan (BOS)

Mon, 2 Nov

6h 45min

1 stop

04:10

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

145 €

WN 956

21:00

Logan (BOS)

Mon, 2 Nov

16h 5min

2 stops

12:05

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

120 €

F9 3511

12:15

Logan (BOS)

Tue, 3 Nov

6h 32min

1 stop

17:47

Chicago Midway International Airport (MDW)

Tue, 3 Nov

120 €

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Tue, 3 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Tue, 3 Nov

98 €

F9 3511

12:39

Logan (BOS)

Wed, 4 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 4 Nov

127 €

WN 813

12:50

Logan (BOS)

Wed, 4 Nov

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

96 €

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Wed, 4 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

97 €

F9 3511

20:39

Logan (BOS)

Thu, 5 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Fri, 6 Nov +1

89 €

WN 816

02:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

108 €

WN 816

18:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

20:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

164 €

WN 787

16:10

Logan (BOS)

Sat, 7 Nov

8h 25min

1 stop

23:35

Chicago Midway International Airport (MDW)

Sat, 7 Nov

118 €

F9 3511

11:27

Logan (BOS)

Sat, 7 Nov

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 7 Nov

106 €

WN 2185

07:05

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Mon, 9 Nov

96 €

WN 813

20:45

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

22:30

Chicago Midway International Airport (MDW)

Mon, 9 Nov

123 €

WN 791

03:30

Logan (BOS)

Tue, 10 Nov

5h 40min

1 stop

08:10

Chicago Midway International Airport (MDW)

Tue, 10 Nov

102 €

F9 3511

20:39

Logan (BOS)

Fri, 13 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Sat, 14 Nov +1

139 €

WN 2758

15:10

Logan (BOS)

Sat, 14 Nov

2h 45min

Direct

16:55

Chicago Midway International Airport (MDW)

Sat, 14 Nov

90 €

WN 819

05:10

Logan (BOS)

Sun, 15 Nov

10h

1 stop

14:10

Chicago Midway International Airport (MDW)

Sun, 15 Nov

143 €

WN 792

05:35

Logan (BOS)

Sun, 15 Nov

9h 15min

2 stops

13:50

Chicago Midway International Airport (MDW)

Sun, 15 Nov

124 €

F9 3511

20:15

Logan (BOS)

Tue, 17 Nov

6h 32min

1 stop

01:47

Chicago Midway International Airport (MDW)

Wed, 18 Nov +1

124 €

F9 3511

20:39

Logan (BOS)

Wed, 18 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Thu, 19 Nov +1

130 €

F9 3511

20:39

Logan (BOS)

Thu, 19 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Fri, 20 Nov +1

130 €

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

81 €

WN 481

15:45

Logan (BOS)

Thu, 26 Nov

9h 35min

1 stop

00:20

Chicago Midway International Airport (MDW)

Fri, 27 Nov +1

127 €

WN 0813

13:05

Logan (BOS)

Thu, 26 Nov

2h 40min

Direct

14:45

Chicago Midway International Airport (MDW)

Thu, 26 Nov

91 €

WN 2185

07:05

Logan (BOS)

Fri, 27 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Fri, 27 Nov

142 €

WN 813

12:50

Logan (BOS)

Tue, 1 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 1 Dec

154 €

F9 1977

11:08

Logan (BOS)

Mon, 7 Dec

10h 34min

1 stop

20:42

Chicago Midway International Airport (MDW)

Mon, 7 Dec

93 €

WN 813

12:50

Logan (BOS)

Tue, 8 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 8 Dec

96 €

F9 1977

11:08

Logan (BOS)

Thu, 10 Dec

10h 34min

1 stop

20:42

Chicago Midway International Airport (MDW)

Thu, 10 Dec

151 €

Direct flight schedule Boston — Chicago Midway International Airport

Direct flights: 9 · First departure: 07:05 · Last departure: 17:55

Departure → arrivalFlightAirport DaysDurationPrice

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

17:55→19:40 Southwest Airlines WN 816 LoganBOS MonTueWedThuFriSatSun 2h 45min

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 121 €

Prices as of 25 October, 11:07 Moscow time

Cheap flights Boston to Chicago Midway International Airport

Frontier Airlines

Mon, Tue, Wed, Thu, Fri, Sat, Sun

Price from

81 €

Southwest Airlines

Mon, Tue, Wed, Thu, Fri, Sat, Sun

Price from

90 €

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 129 €.

Frontier Airlines Average price: 129 € · Flights: 2 · Direct: 0
Southwest Airlines Average price: 136 € · Flights: 28 · Direct: 16
Allegiant Air Average price: 159 € · Flights: 1 · Direct: 0
Jetblue Airways Average price: 1 486 € · 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: 28.

Southwest Airlines Flights: 28 · 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

Trip	Outbound	Return	Outbound + return	Total
Weekend trip	Sat, 12 Dec	Mon, 14 Dec	96 € + 105 €
One week	Wed, 4 Nov	Thu, 12 Nov	82 € + 90 €
Two weeks	Wed, 4 Nov	Thu, 19 Nov	82 € + 83 €

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

Prices as of 25 October, 11:07 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 81 €. Days before departure: 26. 4–7 days before departure tickets cost from 121 €, 1–3 days before — from 133 €.

Before departureDeparture dateDifference from lowestPrice

1–3 days Wed, 28 Oct 64% 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: 10 · Direct: 5
Fri Flights: 8 · Direct: 5
Sat Flights: 6 · Direct: 2
Sun Flights: 7 · Direct: 3

Popular destinations from Boston

All →

BOS

Boston — Lebanon

United States → United States

LEB

from

61 €

BOS

Boston — Rutland

United States → United States

RUT

from

69 €

BOS

Boston — Washington

United States → United States

WAS

from

71 €

BOS

Boston — Montreal

United States → Canada

YMQ

from

74 €

BOS

Boston — Chicago

United States → United States

CHI

from

81 €

Popular destinations to Chicago Midway International Airport

All →

ATL

Atlanta — Chicago

United States → United States

MDW

from

40 €

DFW

Dallas — Chicago

United States → United States

MDW

from

47 €

FLL

Fort Lauderdale — Chicago

United States → United States

MDW

from

47 €

LAS

Las Vegas — Chicago

United States → United States

MDW

from

66 €

PHL

Philadelphia — Chicago

United States → United States

MDW

from

71 €

DEN

Denver — Chicago

United States → United States

MDW

from

74 €

BNA

Nashville — Chicago

United States → United States

MDW

from

85 €

NYC

New York — Chicago

United States → United States

MDW

from

86 €

Cheap flights Boston to Chicago Midway International Airport

Price from: 81 €
Average price: 130 €
Flight time: 2 hours 45 minutes
Distance: 1 379 km
Рейсов в неделю: 32
Airlines: 4
Most frequent flight: WN 816

Prices as of 25 October, 11:06 Moscow time

Airports on the Boston — Chicago Midway International Airport route

From → to	Flights	Direct	Airlines	Price from
LoganBOS Chicago Midway International AirportMDW	32	16	4

Departure airports · Boston

LoganBOS
Pease Air Force BasePSM no flights

Arrival airports · Chicago Midway International Airport

Chicago Midway International AirportMDW ≈ 14 km from the centre

Passenger reviews

No reviews for this route yet

Internet abroad

eSIM · United States

change

3 GB

data

30

days

8 €

change

2 GB

data

15

days

11 €

change

5 GB

data

30

days

12 €

change

3 GB

data

30

days

14 €

change

5 GB

data

30

days

20 €

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 90 €.

The average ticket price Boston Chicago Midway International Airport is 130 €. The cheapest ticket costs 81 €, 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 25 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 81 €. The most expensive month is October, with tickets from 121 €.

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 07:05 (WN 2185, Southwest Airlines), the last one at 17:55 (WN 816, 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.