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 R1 510 (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

Filters

Stops

Direct only 1 stop 2+ stops

Price

R1 510 R27 587 R27 587

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

R3 792

WN 805

12:50

Logan (BOS)

Mon, 26 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Mon, 26 Oct

R1 929

F9 3511

12:57

Logan (BOS)

Mon, 26 Oct

11h 46min

1 stop

23:43

Chicago Midway International Airport (MDW)

Mon, 26 Oct

R2 672

WN 805

14:20

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

15:55

Chicago Midway International Airport (MDW)

Tue, 27 Oct

R1 886

WN 2046

17:55

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Tue, 27 Oct

R1 700

F9 3511

11:12

Logan (BOS)

Tue, 27 Oct

7h 15min

1 stop

17:27

Chicago Midway International Airport (MDW)

Tue, 27 Oct

R2 571

WN 2046

17:55

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Wed, 28 Oct

R1 699

F9 3511

12:39

Logan (BOS)

Wed, 28 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 28 Oct

R2 468

WN 807

12:50

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Wed, 28 Oct

R2 582

WN 805

12:50

Logan (BOS)

Thu, 29 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Thu, 29 Oct

R1 931

F9 3511

12:39

Logan (BOS)

Thu, 29 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Thu, 29 Oct

R2 638

F9 3511

12:39

Logan (BOS)

Fri, 30 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Fri, 30 Oct

R2 240

F9 3511

11:27

Logan (BOS)

Sat, 31 Oct

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 31 Oct

R2 263

WN 792

05:35

Logan (BOS)

Sun, 1 Nov

11h 25min

1 stop

16:00

Chicago Midway International Airport (MDW)

Sun, 1 Nov

R3 225

G4 3473

12:34

Logan (BOS)

Sun, 1 Nov

45h 21min

1 stop

08:55

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

R2 944

F9 3511

12:39

Logan (BOS)

Sun, 1 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Sun, 1 Nov

R3 908

WN 816

02:30

Logan (BOS)

Mon, 2 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Mon, 2 Nov

R5 738

WN 819

13:10

Logan (BOS)

Mon, 2 Nov

10h

1 stop

22:10

Chicago Midway International Airport (MDW)

Mon, 2 Nov

R2 290

F9 3511

12:39

Logan (BOS)

Mon, 2 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Mon, 2 Nov

R2 867

WN 0800

22:25

Logan (BOS)

Mon, 2 Nov

6h 45min

1 stop

04:10

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

R2 692

WN 956

21:00

Logan (BOS)

Mon, 2 Nov

16h 5min

2 stops

12:05

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

R2 234

F9 3511

12:15

Logan (BOS)

Tue, 3 Nov

6h 32min

1 stop

17:47

Chicago Midway International Airport (MDW)

Tue, 3 Nov

R2 274

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Tue, 3 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Tue, 3 Nov

R1 824

F9 3511

12:39

Logan (BOS)

Wed, 4 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 4 Nov

R2 359

WN 813

12:50

Logan (BOS)

Wed, 4 Nov

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

R1 790

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Wed, 4 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

R1 804

F9 3511

20:39

Logan (BOS)

Thu, 5 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Fri, 6 Nov +1

R1 651

WN 816

02:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

R2 000

WN 816

18:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

20:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

R3 038

WN 787

16:10

Logan (BOS)

Sat, 7 Nov

8h 25min

1 stop

23:35

Chicago Midway International Airport (MDW)

Sat, 7 Nov

R2 182

F9 3511

11:27

Logan (BOS)

Sat, 7 Nov

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 7 Nov

R1 963

WN 2185

07:05

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Mon, 9 Nov

R1 790

WN 813

20:45

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

22:30

Chicago Midway International Airport (MDW)

Mon, 9 Nov

R2 279

WN 791

03:30

Logan (BOS)

Tue, 10 Nov

5h 40min

1 stop

08:10

Chicago Midway International Airport (MDW)

Tue, 10 Nov

R1 897

F9 3511

20:39

Logan (BOS)

Fri, 13 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Sat, 14 Nov +1

R2 575

WN 2758

15:10

Logan (BOS)

Sat, 14 Nov

2h 45min

Direct

16:55

Chicago Midway International Airport (MDW)

Sat, 14 Nov

R1 668

WN 819

05:10

Logan (BOS)

Sun, 15 Nov

10h

1 stop

14:10

Chicago Midway International Airport (MDW)

Sun, 15 Nov

R2 651

WN 792

05:35

Logan (BOS)

Sun, 15 Nov

9h 15min

2 stops

13:50

Chicago Midway International Airport (MDW)

Sun, 15 Nov

R2 302

F9 3511

20:15

Logan (BOS)

Tue, 17 Nov

6h 32min

1 stop

01:47

Chicago Midway International Airport (MDW)

Wed, 18 Nov +1

R2 298

F9 3511

20:39

Logan (BOS)

Wed, 18 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Thu, 19 Nov +1

R2 407

F9 3511

20:39

Logan (BOS)

Thu, 19 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Fri, 20 Nov +1

R2 407

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

R1 510

WN 481

15:45

Logan (BOS)

Thu, 26 Nov

9h 35min

1 stop

00:20

Chicago Midway International Airport (MDW)

Fri, 27 Nov +1

R2 364

WN 0813

13:05

Logan (BOS)

Thu, 26 Nov

2h 40min

Direct

14:45

Chicago Midway International Airport (MDW)

Thu, 26 Nov

R1 692

WN 2185

07:05

Logan (BOS)

Fri, 27 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Fri, 27 Nov

R2 637

WN 813

12:50

Logan (BOS)

Tue, 1 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 1 Dec

R2 849

F9 1977

11:08

Logan (BOS)

Mon, 7 Dec

10h 34min

1 stop

20:42

Chicago Midway International Airport (MDW)

Mon, 7 Dec

R1 733

WN 813

12:50

Logan (BOS)

Tue, 8 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 8 Dec

R1 787

F9 1977

11:08

Logan (BOS)

Thu, 10 Dec

10h 34min

1 stop

20:42

Chicago Midway International Airport (MDW)

Thu, 10 Dec

R2 799

WN 816

17:55

Logan (BOS)

Thu, 10 Dec

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Thu, 10 Dec

R1 787

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 R2 240

Prices as of 24 October, 11:05 Moscow time

Cheap flights Boston to Chicago Midway International Airport

Frontier Airlines

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

Price from

R1 510

Southwest Airlines

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

Price from

R1 668

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 R2 392.

Frontier Airlines Average price: R2 392 · Flights: 2 · Direct: 0
Southwest Airlines Average price: R2 528 · Flights: 27 · Direct: 16
Allegiant Air Average price: R2 944 · Flights: 1 · Direct: 0
Jetblue Airways Average price: R27 587 · 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

Trip	Outbound	Return	Outbound + return	Total
Weekend trip	Sat, 12 Dec	Mon, 14 Dec	R1 787 + R1 945
One week	Wed, 4 Nov	Thu, 12 Nov	R1 519 + R1 668
Two weeks	Wed, 4 Nov	Thu, 19 Nov	R1 519 + R1 550

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 R1 510. Days before departure: 26. 4–7 days before departure tickets cost from R2 240, 1–3 days before — from R2 468.

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: 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

R1 132

BOS

Boston — Rutland

United States → United States

RUT

from

R1 287

BOS

Boston — Washington

United States → United States

WAS

from

R1 320

BOS

Boston — Chicago

United States → United States

CHI

from

R1 510

BOS

Boston — Orlando

United States → United States

ORL

from

R1 547

BOS

Boston — Philadelphia

United States → United States

PHL

from

R1 559

Popular destinations to Chicago Midway International Airport

All →

ATL

Atlanta — Chicago

United States → United States

MDW

from

R743

FLL

Fort Lauderdale — Chicago

United States → United States

MDW

from

R878

DFW

Dallas — Chicago

United States → United States

MDW

from

R893

PHL

Philadelphia — Chicago

United States → United States

MDW

from

R1 324

DEN

Denver — Chicago

United States → United States

MDW

from

R1 377

BNA

Nashville — Chicago

United States → United States

MDW

from

R1 585

NYC

New York — Chicago

United States → United States

MDW

from

R1 591

LAX

Los Angeles — Chicago

United States → United States

MDW

from

R1 650

Cheap flights Boston to Chicago Midway International Airport

Price from: R1 510
Average price: R2 437
Flight time: 2 hours 45 minutes
Distance: 1 379 km
Рейсов в неделю: 31
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	30	15	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

R149

change

2 GB

data

15

days

R207

change

5 GB

data

30

days

R232

change

3 GB

data

30

days

R265

change

5 GB

data

30

days

R373

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 R1 668.

The average ticket price Boston Chicago Midway International Airport is R2 437. The cheapest ticket costs R1 510, 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 R1 510. The most expensive month is October, with tickets from R2 240.

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.