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: 30. Flight time: 2 hours 45 minutes. Distance: 1379 km. Tickets from TSh224 767 (departure 20 November).

Prices updated on 26 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

TSh224 767 TSh4 107 760 TSh4 107 760

Airlines

Allegiant Air Frontier Airlines Jetblue Airways Southwest Airlines

WN 805

12:50

Logan (BOS)

Mon, 26 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Mon, 26 Oct

TSh287 237

F9 3511

12:57

Logan (BOS)

Mon, 26 Oct

11h 46min

1 stop

23:43

Chicago Midway International Airport (MDW)

Mon, 26 Oct

TSh395 394

WN 805

14:20

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

15:55

Chicago Midway International Airport (MDW)

Tue, 27 Oct

TSh280 775

WN 2046

17:55

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Tue, 27 Oct

TSh253 185

F9 3511

11:12

Logan (BOS)

Tue, 27 Oct

7h 15min

1 stop

17:27

Chicago Midway International Airport (MDW)

Tue, 27 Oct

TSh382 809

WN 2046

17:55

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Wed, 28 Oct

TSh252 940

F9 3511

12:39

Logan (BOS)

Wed, 28 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 28 Oct

TSh367 498

WN 807

12:50

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Wed, 28 Oct

TSh384 524

WN 805

12:50

Logan (BOS)

Thu, 29 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Thu, 29 Oct

TSh287 573

F9 3511

12:39

Logan (BOS)

Thu, 29 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Thu, 29 Oct

TSh392 761

F9 3511

12:39

Logan (BOS)

Fri, 30 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Fri, 30 Oct

TSh333 507

F9 3511

11:27

Logan (BOS)

Sat, 31 Oct

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 31 Oct

TSh336 906

WN 792

05:35

Logan (BOS)

Sun, 1 Nov

11h 25min

1 stop

16:00

Chicago Midway International Airport (MDW)

Sun, 1 Nov

TSh480 218

G4 3473

12:34

Logan (BOS)

Sun, 1 Nov

45h 21min

1 stop

08:55

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

TSh438 296

F9 3511

12:39

Logan (BOS)

Sun, 1 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Sun, 1 Nov

TSh581 853

WN 816

02:30

Logan (BOS)

Mon, 2 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Mon, 2 Nov

TSh854 330

WN 819

13:10

Logan (BOS)

Mon, 2 Nov

10h

1 stop

22:10

Chicago Midway International Airport (MDW)

Mon, 2 Nov

TSh340 979

F9 3511

12:39

Logan (BOS)

Mon, 2 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Mon, 2 Nov

TSh426 874

WN 0800

22:25

Logan (BOS)

Mon, 2 Nov

6h 45min

1 stop

04:10

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

TSh400 784

WN 956

21:00

Logan (BOS)

Mon, 2 Nov

16h 5min

2 stops

12:05

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

TSh332 711

F9 3511

12:15

Logan (BOS)

Tue, 3 Nov

6h 32min

1 stop

17:47

Chicago Midway International Airport (MDW)

Tue, 3 Nov

TSh332 098

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Tue, 3 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Tue, 3 Nov

TSh271 589

F9 3511

12:39

Logan (BOS)

Wed, 4 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 4 Nov

TSh343 827

WN 813

12:50

Logan (BOS)

Wed, 4 Nov

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

TSh266 475

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Wed, 4 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

TSh268 680

F9 3511

20:39

Logan (BOS)

Thu, 5 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Fri, 6 Nov +1

TSh245 835

WN 816

02:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

TSh297 771

WN 816

18:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

20:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

TSh452 413

WN 787

16:10

Logan (BOS)

Sat, 7 Nov

8h 25min

1 stop

23:35

Chicago Midway International Airport (MDW)

Sat, 7 Nov

TSh324 841

F9 3511

11:27

Logan (BOS)

Sat, 7 Nov

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 7 Nov

TSh292 228

WN 2185

07:05

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Mon, 9 Nov

TSh266 475

WN 813

20:45

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

22:30

Chicago Midway International Airport (MDW)

Mon, 9 Nov

TSh339 294

WN 791

03:30

Logan (BOS)

Tue, 10 Nov

5h 40min

1 stop

08:10

Chicago Midway International Airport (MDW)

Tue, 10 Nov

TSh282 460

F9 3511

20:39

Logan (BOS)

Fri, 13 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Sat, 14 Nov +1

TSh383 360

WN 2758

15:10

Logan (BOS)

Sat, 14 Nov

2h 45min

Direct

16:55

Chicago Midway International Airport (MDW)

Sat, 14 Nov

TSh248 408

WN 819

05:10

Logan (BOS)

Sun, 15 Nov

10h

1 stop

14:10

Chicago Midway International Airport (MDW)

Sun, 15 Nov

TSh394 690

WN 792

05:35

Logan (BOS)

Sun, 15 Nov

9h 15min

2 stops

13:50

Chicago Midway International Airport (MDW)

Sun, 15 Nov

TSh342 755

F9 3511

20:15

Logan (BOS)

Tue, 17 Nov

6h 32min

1 stop

01:47

Chicago Midway International Airport (MDW)

Wed, 18 Nov +1

TSh342 142

F9 3511

20:39

Logan (BOS)

Wed, 18 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Thu, 19 Nov +1

TSh358 372

F9 3511

20:39

Logan (BOS)

Thu, 19 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Fri, 20 Nov +1

TSh358 403

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

TSh224 767

WN 816

22:25

Logan (BOS)

Wed, 25 Nov

3h

Direct

00:25

Chicago Midway International Airport (MDW)

Thu, 26 Nov +1

TSh424 853

WN 481

15:45

Logan (BOS)

Thu, 26 Nov

9h 35min

1 stop

00:20

Chicago Midway International Airport (MDW)

Fri, 27 Nov +1

TSh352 064

WN 0813

13:05

Logan (BOS)

Thu, 26 Nov

2h 40min

Direct

14:45

Chicago Midway International Airport (MDW)

Thu, 26 Nov

TSh251 868

WN 2185

07:05

Logan (BOS)

Fri, 27 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Fri, 27 Nov

TSh392 608

WN 813

12:50

Logan (BOS)

Tue, 1 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 1 Dec

TSh424 271

F9 1977

11:08

Logan (BOS)

Mon, 7 Dec

10h 34min

1 stop

20:42

Chicago Midway International Airport (MDW)

Mon, 7 Dec

TSh258 054

WN 813

12:50

Logan (BOS)

Tue, 8 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 8 Dec

TSh266 077

F9 1977

11:08

Logan (BOS)

Thu, 10 Dec

10h 34min

1 stop

20:42

Chicago Midway International Airport (MDW)

Thu, 10 Dec

TSh416 738

WN 816

17:55

Logan (BOS)

Thu, 10 Dec

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Thu, 10 Dec

TSh266 077

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 TSh333 507

Prices as of 26 October, 11:04 Moscow time

Cheap flights Boston to Chicago Midway International Airport

Frontier Airlines

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

Price from

TSh224 767

Southwest Airlines

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

Price from

TSh248 408

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 TSh355 371.

Frontier Airlines Average price: TSh355 371 · Flights: 2 · Direct: 0
Southwest Airlines Average price: TSh369 947 · Flights: 26 · Direct: 14
Allegiant Air Average price: TSh438 296 · Flights: 1 · Direct: 0
Jetblue Airways Average price: TSh4 107 760 · 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: 26.

Southwest Airlines Flights: 26 · Direct: 14
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	TSh266 077 + TSh289 595
One week	Wed, 4 Nov	Thu, 12 Nov	TSh226 115 + TSh248 408
Two weeks	Wed, 4 Nov	Thu, 19 Nov	TSh226 115 + TSh230 739

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

Prices as of 26 October, 11:04 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 TSh224 767. Days before departure: 25. 4–7 days before departure tickets cost from TSh333 507, 1–3 days before — from TSh367 498.

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 Sun (5).

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: 5 · Direct: 1

Popular destinations from Boston

All →

BOS

Boston — Washington

United States → United States

WAS

from

TSh141 414

BOS

Boston — Lebanon

United States → United States

LEB

from

TSh168 484

BOS

Boston — Rutland

United States → United States

RUT

from

TSh191 603

BOS

Boston — Montreal

United States → Canada

YMQ

from

TSh204 005

BOS

Boston — Chicago

United States → United States

CHI

from

TSh224 767

Popular destinations to Chicago Midway International Airport

All →

ATL

Atlanta — Chicago

United States → United States

MDW

from

TSh110 638

FLL

Fort Lauderdale — Chicago

United States → United States

MDW

from

TSh130 726

DFW

Dallas — Chicago

United States → United States

MDW

from

TSh133 023

LAS

Las Vegas — Chicago

United States → United States

MDW

from

TSh181 284

PHL

Philadelphia — Chicago

United States → United States

MDW

from

TSh197 085

DEN

Denver — Chicago

United States → United States

MDW

from

TSh204 985

BNA

Nashville — Chicago

United States → United States

MDW

from

TSh236 067

NYC

New York — Chicago

United States → United States

MDW

from

TSh236 894

Cheap flights Boston to Chicago Midway International Airport

Price from: TSh224 767
Average price: TSh358 372
Flight time: 2 hours 45 minutes
Distance: 1 379 km
Рейсов в неделю: 30
Airlines: 4
Most frequent flight: WN 816

Prices as of 26 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	30	14	4

Departure airports · Boston

LoganBOS
Portsmouth International at Pease AirportPSM 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

TSh22 196

change

2 GB

data

15

days

TSh30 828

change

5 GB

data

30

days

TSh34 528

change

3 GB

data

30

days

TSh39 460

change

5 GB

data

30

days

TSh55 491

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 TSh248 408.

The average ticket price Boston Chicago Midway International Airport is TSh358 372. The cheapest ticket costs TSh224 767, 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 26 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 TSh224 767. The most expensive month is December, with tickets from TSh255 849.

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.