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: 31. Flight time: 2 hours 45 minutes. Distance: 1379 km. Tickets from C$140 (departure 5 November).

Prices updated on 23 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

Filters

Stops

Direct only 1 stop 2+ stops

Price

C$140 C$2 335 C$2 335

Airlines

Allegiant Air Frontier Airlines Jetblue Airways Southwest Airlines

WN 909

22:00

Logan (BOS)

Fri, 23 Oct

2h 40min

Direct

23:40

Chicago Midway International Airport (MDW)

Fri, 23 Oct

C$276

WN 1346

09:40

Logan (BOS)

Sat, 24 Oct

2h 35min

Direct

11:15

Chicago Midway International Airport (MDW)

Sat, 24 Oct

C$276

WN 4568

13:10

Logan (BOS)

Sun, 25 Oct

2h 35min

Direct

14:45

Chicago Midway International Airport (MDW)

Sun, 25 Oct

C$321

WN 805

12:50

Logan (BOS)

Mon, 26 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Mon, 26 Oct

C$163

F9 3511

12:57

Logan (BOS)

Mon, 26 Oct

11h 46min

1 stop

23:43

Chicago Midway International Airport (MDW)

Mon, 26 Oct

C$228

WN 805

14:20

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

15:55

Chicago Midway International Airport (MDW)

Tue, 27 Oct

C$160

WN 2046

17:55

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Tue, 27 Oct

C$144

F9 3511

11:12

Logan (BOS)

Tue, 27 Oct

7h 15min

1 stop

17:27

Chicago Midway International Airport (MDW)

Tue, 27 Oct

C$218

WN 2046

17:55

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Wed, 28 Oct

C$144

F9 3511

12:39

Logan (BOS)

Wed, 28 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 28 Oct

C$209

WN 807

12:50

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Wed, 28 Oct

C$219

WN 805

12:50

Logan (BOS)

Thu, 29 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Thu, 29 Oct

C$163

F9 3511

12:39

Logan (BOS)

Thu, 29 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Thu, 29 Oct

C$223

F9 3511

12:39

Logan (BOS)

Fri, 30 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Fri, 30 Oct

C$190

F9 3511

11:27

Logan (BOS)

Sat, 31 Oct

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 31 Oct

C$192

WN 792

05:35

Logan (BOS)

Sun, 1 Nov

11h 25min

1 stop

16:00

Chicago Midway International Airport (MDW)

Sun, 1 Nov

C$273

G4 3473

12:34

Logan (BOS)

Sun, 1 Nov

45h 21min

1 stop

08:55

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

C$249

F9 3511

12:39

Logan (BOS)

Sun, 1 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Sun, 1 Nov

C$331

WN 816

02:30

Logan (BOS)

Mon, 2 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Mon, 2 Nov

C$486

WN 819

13:10

Logan (BOS)

Mon, 2 Nov

10h

1 stop

22:10

Chicago Midway International Airport (MDW)

Mon, 2 Nov

C$194

F9 3511

12:39

Logan (BOS)

Mon, 2 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Mon, 2 Nov

C$245

WN 0800

22:25

Logan (BOS)

Mon, 2 Nov

6h 45min

1 stop

04:10

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

C$228

WN 956

21:00

Logan (BOS)

Mon, 2 Nov

16h 5min

2 stops

12:05

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

C$189

F9 3511

12:15

Logan (BOS)

Tue, 3 Nov

6h 32min

1 stop

17:47

Chicago Midway International Airport (MDW)

Tue, 3 Nov

C$192

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Tue, 3 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Tue, 3 Nov

C$154

F9 3511

12:39

Logan (BOS)

Wed, 4 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 4 Nov

C$200

WN 813

12:50

Logan (BOS)

Wed, 4 Nov

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

C$151

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Wed, 4 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

C$153

F9 3511 Best price

20:39

Logan (BOS)

Thu, 5 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Fri, 6 Nov +1

C$140

WN 816

02:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

C$169

WN 816

18:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

20:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

C$257

WN 787

16:10

Logan (BOS)

Sat, 7 Nov

8h 25min

1 stop

23:35

Chicago Midway International Airport (MDW)

Sat, 7 Nov

C$185

F9 3511

11:27

Logan (BOS)

Sat, 7 Nov

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 7 Nov

C$169

WN 2185

07:05

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Mon, 9 Nov

C$151

WN 813

20:45

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

22:30

Chicago Midway International Airport (MDW)

Mon, 9 Nov

C$193

WN 791

03:30

Logan (BOS)

Tue, 10 Nov

5h 40min

1 stop

08:10

Chicago Midway International Airport (MDW)

Tue, 10 Nov

C$161

F9 3511

20:39

Logan (BOS)

Fri, 13 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Sat, 14 Nov +1

C$218

WN 2758

15:10

Logan (BOS)

Sat, 14 Nov

2h 45min

Direct

16:55

Chicago Midway International Airport (MDW)

Sat, 14 Nov

C$141

WN 819

05:10

Logan (BOS)

Sun, 15 Nov

10h

1 stop

14:10

Chicago Midway International Airport (MDW)

Sun, 15 Nov

C$224

WN 792

05:35

Logan (BOS)

Sun, 15 Nov

9h 15min

2 stops

13:50

Chicago Midway International Airport (MDW)

Sun, 15 Nov

C$195

F9 3511

20:15

Logan (BOS)

Tue, 17 Nov

6h 32min

1 stop

01:47

Chicago Midway International Airport (MDW)

Wed, 18 Nov +1

C$195

F9 3511

20:39

Logan (BOS)

Wed, 18 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Thu, 19 Nov +1

C$204

F9 3511

20:39

Logan (BOS)

Thu, 19 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Fri, 20 Nov +1

C$204

WN 481

15:45

Logan (BOS)

Thu, 26 Nov

9h 35min

1 stop

00:20

Chicago Midway International Airport (MDW)

Fri, 27 Nov +1

C$200

WN 0813

13:05

Logan (BOS)

Thu, 26 Nov

2h 40min

Direct

14:45

Chicago Midway International Airport (MDW)

Thu, 26 Nov

C$143

WN 2185

07:05

Logan (BOS)

Fri, 27 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Fri, 27 Nov

C$223

WN 813

12:50

Logan (BOS)

Tue, 1 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 1 Dec

C$241

F9 1977

11:08

Logan (BOS)

Mon, 7 Dec

10h 34min

1 stop

20:42

Chicago Midway International Airport (MDW)

Mon, 7 Dec

C$147

WN 813

12:50

Logan (BOS)

Tue, 8 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 8 Dec

C$151

F9 1977

11:08

Logan (BOS)

Thu, 10 Dec

10h 34min

1 stop

20:42

Chicago Midway International Airport (MDW)

Thu, 10 Dec

C$237

Direct flight schedule Boston — Chicago Midway International Airport

Direct flights: 7 · 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

07:30→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

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 C$190

Prices as of 23 October, 11:05 Moscow time

Cheap flights Boston to Chicago Midway International Airport

Southwest Airlines

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

Price from

C$141

Frontier Airlines

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

Price from

C$169

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 C$207.

Frontier Airlines Average price: C$207 · Flights: 2 · Direct: 0
Southwest Airlines Average price: C$219 · Flights: 28 · Direct: 17
Allegiant Air Average price: C$249 · Flights: 1 · Direct: 0
Jetblue Airways Average price: C$2 335 · 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: 17
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	C$151 + C$165
One week	Wed, 4 Nov	Thu, 12 Nov	C$129 + C$141
Two weeks	Wed, 4 Nov	Thu, 19 Nov	C$129 + C$131

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

Prices as of 23 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 Thu, 5 Nov — from C$140. Days before departure: 12. 4–7 days before departure tickets cost from C$190, 1–3 days before — from C$218.

Before departureDeparture dateDifference from lowestPrice

1–3 days Tue, 27 Oct 56% more

4–7 days Fri, 30 Oct 36% more

8–14 days Thu, 5 Nov cheapest

15–21 days Sat, 14 Nov 1% more

22–30 days Tue, 17 Nov 39% more

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: 8 · Direct: 4
Fri Flights: 9 · Direct: 6
Sat Flights: 7 · Direct: 3
Sun Flights: 6 · Direct: 2

Popular destinations from Boston

All →

BOS

Boston — Lebanon

United States → United States

LEB

from

C$96

BOS

Boston — Rutland

United States → United States

RUT

from

C$109

BOS

Boston — Washington

United States → United States

WAS

from

C$112

BOS

Boston — Philadelphia

United States → United States

PHL

from

C$134

BOS

Boston — Orlando

United States → United States

ORL

from

C$137

BOS

Boston — San Jose

United States → United States

SJC

from

C$144

Popular destinations to Chicago Midway International Airport

All →

ATL

Atlanta — Chicago

United States → United States

MDW

from

C$63

FLL

Fort Lauderdale — Chicago

United States → United States

MDW

from

C$74

DFW

Dallas — Chicago

United States → United States

MDW

from

C$76

PHL

Philadelphia — Chicago

United States → United States

MDW

from

C$112

DEN

Denver — Chicago

United States → United States

MDW

from

C$121

BNA

Nashville — Chicago

United States → United States

MDW

from

C$134

LAX

Los Angeles — Chicago

United States → United States

MDW

from

C$140

TPA

Tampa — Chicago

United States → United States

MDW

from

C$145

NYC

New York — Chicago

United States → United States

MDW

from

C$145

Cheap flights Boston to Chicago Midway International Airport

Price from: C$140
Average price: C$209
Flight time: 2 hours 45 minutes
Distance: 1 379 km
Рейсов в неделю: 31
Airlines: 4
Most frequent flight: WN 816

Prices as of 23 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	32	17	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

C$13

change

2 GB

data

15

days

C$18

change

5 GB

data

30

days

C$20

change

3 GB

data

30

days

C$22

change

5 GB

data

30

days

C$32

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 C$141.

The average ticket price Boston Chicago Midway International Airport is C$209. The cheapest ticket costs C$140, operated by Frontier Airlines, flight F9 3511, departing Boston on 5 November at 20:39, arriving Chicago Midway International Airport on 6 November at 07:47. Prices as of 23 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 11 hours.

Based on prices for the coming months, the cheapest month to fly is November: tickets from C$140. The most expensive month is October, with tickets from C$190.

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.