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 KSh12 197 (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

KSh12 197 KSh203 803 KSh203 803

Airlines

Allegiant Air Frontier Airlines Jetblue Airways Southwest Airlines

WN 805

05:50

Logan (BOS)

Fri, 23 Oct

2h 35min

Direct

07:25

Chicago Midway International Airport (MDW)

Fri, 23 Oct

KSh26 006

F9 3511

12:57

Logan (BOS)

Fri, 23 Oct

11h 46min

1 stop

23:43

Chicago Midway International Airport (MDW)

Fri, 23 Oct

KSh18 703

WN 909

22:00

Logan (BOS)

Fri, 23 Oct

2h 40min

Direct

23:40

Chicago Midway International Airport (MDW)

Fri, 23 Oct

KSh24 088

WN 1346

09:40

Logan (BOS)

Sat, 24 Oct

2h 35min

Direct

11:15

Chicago Midway International Airport (MDW)

Sat, 24 Oct

KSh24 088

WN 4568

13:10

Logan (BOS)

Sun, 25 Oct

2h 35min

Direct

14:45

Chicago Midway International Airport (MDW)

Sun, 25 Oct

KSh28 016

WN 805

12:50

Logan (BOS)

Mon, 26 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Mon, 26 Oct

KSh14 251

F9 3511

12:57

Logan (BOS)

Mon, 26 Oct

11h 46min

1 stop

23:43

Chicago Midway International Airport (MDW)

Mon, 26 Oct

KSh19 897

WN 805

14:20

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

15:55

Chicago Midway International Airport (MDW)

Tue, 27 Oct

KSh13 930

WN 2046

17:55

Logan (BOS)

Tue, 27 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Tue, 27 Oct

KSh12 562

F9 3511

11:12

Logan (BOS)

Tue, 27 Oct

7h 15min

1 stop

17:27

Chicago Midway International Airport (MDW)

Tue, 27 Oct

KSh18 993

WN 2046

17:55

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

19:30

Chicago Midway International Airport (MDW)

Wed, 28 Oct

KSh12 549

F9 3511

12:39

Logan (BOS)

Wed, 28 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 28 Oct

KSh18 233

WN 807

12:50

Logan (BOS)

Wed, 28 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Wed, 28 Oct

KSh19 078

WN 805

12:50

Logan (BOS)

Thu, 29 Oct

2h 35min

Direct

14:25

Chicago Midway International Airport (MDW)

Thu, 29 Oct

KSh14 268

F9 3511

12:39

Logan (BOS)

Thu, 29 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Thu, 29 Oct

KSh19 486

F9 3511

12:39

Logan (BOS)

Fri, 30 Oct

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Fri, 30 Oct

KSh16 547

F9 3511

11:27

Logan (BOS)

Sat, 31 Oct

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 31 Oct

KSh16 715

WN 792

05:35

Logan (BOS)

Sun, 1 Nov

11h 25min

1 stop

16:00

Chicago Midway International Airport (MDW)

Sun, 1 Nov

KSh23 826

G4 3473

12:34

Logan (BOS)

Sun, 1 Nov

45h 21min

1 stop

08:55

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

KSh21 746

F9 3511

12:39

Logan (BOS)

Sun, 1 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Sun, 1 Nov

KSh28 868

WN 816

02:30

Logan (BOS)

Mon, 2 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Mon, 2 Nov

KSh42 387

WN 819

13:10

Logan (BOS)

Mon, 2 Nov

10h

1 stop

22:10

Chicago Midway International Airport (MDW)

Mon, 2 Nov

KSh16 917

F9 3511

12:39

Logan (BOS)

Mon, 2 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Mon, 2 Nov

KSh21 358

WN 0800

22:25

Logan (BOS)

Mon, 2 Nov

6h 45min

1 stop

04:10

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

KSh19 885

WN 956

21:00

Logan (BOS)

Mon, 2 Nov

16h 5min

2 stops

12:05

Chicago Midway International Airport (MDW)

Tue, 3 Nov +1

KSh16 507

F9 3511

12:15

Logan (BOS)

Tue, 3 Nov

6h 32min

1 stop

17:47

Chicago Midway International Airport (MDW)

Tue, 3 Nov

KSh16 799

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Tue, 3 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Tue, 3 Nov

KSh13 475

F9 3511

12:39

Logan (BOS)

Wed, 4 Nov

12h 8min

1 stop

23:47

Chicago Midway International Airport (MDW)

Wed, 4 Nov

KSh17 428

WN 813

12:50

Logan (BOS)

Wed, 4 Nov

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

KSh13 221

WN 816 🔥 Hot deal

17:55

Logan (BOS)

Wed, 4 Nov

2h 45min

Direct

19:40

Chicago Midway International Airport (MDW)

Wed, 4 Nov

KSh13 330

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

KSh12 197

WN 816

02:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

04:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

KSh14 774

WN 816

18:30

Logan (BOS)

Fri, 6 Nov

2h 45min

Direct

20:15

Chicago Midway International Airport (MDW)

Fri, 6 Nov

KSh22 446

WN 787

16:10

Logan (BOS)

Sat, 7 Nov

8h 25min

1 stop

23:35

Chicago Midway International Airport (MDW)

Sat, 7 Nov

KSh16 117

F9 3511

11:27

Logan (BOS)

Sat, 7 Nov

7h 20min

1 stop

17:47

Chicago Midway International Airport (MDW)

Sat, 7 Nov

KSh14 723

WN 2185

07:05

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Mon, 9 Nov

KSh13 221

WN 813

20:45

Logan (BOS)

Mon, 9 Nov

2h 45min

Direct

22:30

Chicago Midway International Airport (MDW)

Mon, 9 Nov

KSh16 834

WN 791

03:30

Logan (BOS)

Tue, 10 Nov

5h 40min

1 stop

08:10

Chicago Midway International Airport (MDW)

Tue, 10 Nov

KSh14 014

F9 3511

20:39

Logan (BOS)

Fri, 13 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Sat, 14 Nov +1

KSh19 020

WN 2758

15:10

Logan (BOS)

Sat, 14 Nov

2h 45min

Direct

16:55

Chicago Midway International Airport (MDW)

Sat, 14 Nov

KSh12 325

WN 819

05:10

Logan (BOS)

Sun, 15 Nov

10h

1 stop

14:10

Chicago Midway International Airport (MDW)

Sun, 15 Nov

KSh19 582

WN 792

05:35

Logan (BOS)

Sun, 15 Nov

9h 15min

2 stops

13:50

Chicago Midway International Airport (MDW)

Sun, 15 Nov

KSh17 005

F9 3511

20:15

Logan (BOS)

Tue, 17 Nov

6h 32min

1 stop

01:47

Chicago Midway International Airport (MDW)

Wed, 18 Nov +1

KSh16 975

F9 3511

20:39

Logan (BOS)

Wed, 18 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Thu, 19 Nov +1

KSh17 780

F9 3511

20:39

Logan (BOS)

Thu, 19 Nov

12h 8min

1 stop

07:47

Chicago Midway International Airport (MDW)

Fri, 20 Nov +1

KSh17 782

WN 481

15:45

Logan (BOS)

Thu, 26 Nov

9h 35min

1 stop

00:20

Chicago Midway International Airport (MDW)

Fri, 27 Nov +1

KSh17 467

WN 0813

13:05

Logan (BOS)

Thu, 26 Nov

2h 40min

Direct

14:45

Chicago Midway International Airport (MDW)

Thu, 26 Nov

KSh12 496

WN 2185

07:05

Logan (BOS)

Fri, 27 Nov

2h 45min

Direct

08:50

Chicago Midway International Airport (MDW)

Fri, 27 Nov

KSh19 479

WN 813

12:50

Logan (BOS)

Tue, 1 Dec

2h 50min

Direct

14:40

Chicago Midway International Airport (MDW)

Tue, 1 Dec

KSh21 050

F9 1977

11:08

Logan (BOS)

Mon, 7 Dec

10h 34min

1 stop

20:42

Chicago Midway International Airport (MDW)

Mon, 7 Dec

KSh12 803

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 KSh16 547

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

KSh12 325

Frontier Airlines

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

Price from

KSh14 723

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 KSh18 078.

Frontier Airlines Average price: KSh18 078 · Flights: 2 · Direct: 0
Southwest Airlines Average price: KSh19 095 · Flights: 28 · Direct: 17
Allegiant Air Average price: KSh21 746 · Flights: 1 · Direct: 0
Jetblue Airways Average price: KSh203 803 · 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	KSh13 201 + KSh14 368
One week	Wed, 4 Nov	Thu, 12 Nov	KSh11 218 + KSh12 325
Two weeks	Wed, 4 Nov	Thu, 19 Nov	KSh11 218 + KSh11 448

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 KSh12 197. Days before departure: 13. 4–7 days before departure tickets cost from KSh16 547, 1–3 days before — from KSh19 897.

Before departureDeparture dateDifference from lowestPrice

1–3 days Mon, 26 Oct 63% more

4–7 days Fri, 30 Oct 36% more

8–14 days Thu, 5 Nov cheapest

15–21 days Mon, 9 Nov 8% more

22–30 days Sat, 14 Nov 1% 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

KSh8 359

BOS

Boston — Rutland

United States → United States

RUT

from

KSh9 506

BOS

Boston — Washington

United States → United States

WAS

from

KSh9 752

BOS

Boston — Philadelphia

United States → United States

PHL

from

KSh11 696

BOS

Boston — Orlando

United States → United States

ORL

from

KSh11 934

BOS

Boston — San Jose

United States → United States

SJC

from

KSh12 574

Popular destinations to Chicago Midway International Airport

All →

ATL

Atlanta — Chicago

United States → United States

MDW

from

KSh5 489

FLL

Fort Lauderdale — Chicago

United States → United States

MDW

from

KSh6 486

DFW

Dallas — Chicago

United States → United States

MDW

from

KSh6 600

PHL

Philadelphia — Chicago

United States → United States

MDW

from

KSh9 778

DEN

Denver — Chicago

United States → United States

MDW

from

KSh10 561

BNA

Nashville — Chicago

United States → United States

MDW

from

KSh11 712

LAX

Los Angeles — Chicago

United States → United States

MDW

from

KSh12 192

TPA

Tampa — Chicago

United States → United States

MDW

from

KSh12 675

NYC

New York — Chicago

United States → United States

MDW

from

KSh12 695

Cheap flights Boston to Chicago Midway International Airport

Price from: KSh12 197
Average price: KSh18 277
Flight time: 2 hours 45 minutes
Distance: 1 379 km
Рейсов в неделю: 32
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
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

KSh1 109

change

2 GB

data

15

days

KSh1 541

change

5 GB

data

30

days

KSh1 726

change

3 GB

data

30

days

KSh1 972

change

5 GB

data

30

days

KSh2 773

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 KSh12 325.

The average ticket price Boston Chicago Midway International Airport is KSh18 277. The cheapest ticket costs KSh12 197, 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 KSh12 197. The most expensive month is October, with tickets from KSh16 547.

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.