Cheap Flights from Boston (BOS) to Chicago (MDW)

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Popular airlines from Logan International Airport (BOS) to Chicago Midway Airport (MDW)

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Cheap Flights from Boston to Chicago (BOS-MDW)

Prices were available within the past 7 days and start at for one-way flights and AED1,350 for round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED1,350 Roundtrip, found 6 days ago
AED1,350
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED1,350 found 6 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED1,390 Roundtrip, found 6 days ago
AED1,390
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED1,390 found 6 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED1,540 Roundtrip, found 6 days ago
AED1,540
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED1,540 found 6 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED1,580 Roundtrip, found 6 days ago
AED1,580
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED1,580 found 6 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED1,640 Roundtrip, found 6 days ago
AED1,640
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED1,640 found 6 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED1,690 Roundtrip, found 6 days ago
AED1,690
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED1,690 found 6 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED1,830 Roundtrip, found 6 days ago
AED1,830
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED1,830 found 6 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED1,870 Roundtrip, found 6 days ago
AED1,870
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED1,870 found 6 days ago
Delta
Tuesday, 21 April, 2026 - Friday, 1 May, 2026
BOS
Boston
MDW
Chicago
AED1,900 Roundtrip, found 5 days ago
AED1,900
Roundtrip
found 5 days ago
Select Delta flight, departing Tuesday, 21 April, 2026 from Boston to Chicago, returning Friday, 1 May, 2026, priced at AED1,900 found 5 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED1,940 Roundtrip, found 6 days ago
AED1,940
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED1,940 found 6 days ago
Delta
Tuesday, 21 April, 2026 - Friday, 1 May, 2026
BOS
Boston
MDW
Chicago
AED2,050 Roundtrip, found 5 days ago
AED2,050
Roundtrip
found 5 days ago
Select Delta flight, departing Tuesday, 21 April, 2026 from Boston to Chicago, returning Friday, 1 May, 2026, priced at AED2,050 found 5 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED2,130 Roundtrip, found 6 days ago
AED2,130
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED2,130 found 6 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED2,160 Roundtrip, found 6 days ago
AED2,160
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED2,160 found 6 days ago
Delta
Tuesday, 21 April, 2026 - Friday, 1 May, 2026
BOS
Boston
MDW
Chicago
AED2,240 Roundtrip, found 5 days ago
AED2,240
Roundtrip
found 5 days ago
Select Delta flight, departing Tuesday, 21 April, 2026 from Boston to Chicago, returning Friday, 1 May, 2026, priced at AED2,240 found 5 days ago
Delta
Tuesday, 21 April, 2026 - Friday, 1 May, 2026
BOS
Boston
MDW
Chicago
AED2,270 Roundtrip, found 5 days ago
AED2,270
Roundtrip
found 5 days ago
Select Delta flight, departing Tuesday, 21 April, 2026 from Boston to Chicago, returning Friday, 1 May, 2026, priced at AED2,270 found 5 days ago
Delta
Tuesday, 21 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED2,310 Roundtrip, found 2 days ago
AED2,310
Roundtrip
found 2 days ago
Select Delta flight, departing Tuesday, 21 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED2,310 found 2 days ago
Delta
Tuesday, 21 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED2,340 Roundtrip, found 2 days ago
AED2,340
Roundtrip
found 2 days ago
Select Delta flight, departing Tuesday, 21 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED2,340 found 2 days ago
Delta
Tuesday, 21 April, 2026 - Friday, 1 May, 2026
BOS
Boston
MDW
Chicago
AED2,420 Roundtrip, found 5 days ago
AED2,420
Roundtrip
found 5 days ago
Select Delta flight, departing Tuesday, 21 April, 2026 from Boston to Chicago, returning Friday, 1 May, 2026, priced at AED2,420 found 5 days ago
Delta
Tuesday, 21 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED2,450 Roundtrip, found 2 days ago
AED2,450
Roundtrip
found 2 days ago
Select Delta flight, departing Tuesday, 21 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED2,450 found 2 days ago
Delta
Wednesday, 22 April, 2026 - Tuesday, 28 April, 2026
BOS
Boston
MDW
Chicago
AED2,490 Roundtrip, found 6 days ago
AED2,490
Roundtrip
found 6 days ago
Select Delta flight, departing Wednesday, 22 April, 2026 from Boston to Chicago, returning Tuesday, 28 April, 2026, priced at AED2,490 found 6 days ago

Frequently asked questions

Is it cheaper to buy a plane ticket from Logan Intl. Airport (BOS) to Midway Intl. Airport (MDW) last minute?
When it comes to booking your flights, being prepared pays dividends. While it's possible to pick up a last-minute deal on a Logan Intl. Airport to Midway Airport flight, fares usually don't get cheaper as the date of departure nears. Based on flight pricing and demand studies in 2022, we have found that the sweet spot to lock in a domestic flight is between 28 – 35 days in advance. For international journeys it's three to four months.
What airports do you fly into for Chicago from Boston?
With Midway Intl. Airport (MDW), O'Hare Intl. Airport (ORD) and Lewis University Airport (LOT) to pick from, flying from Boston to Chicago is a piece of cake. The city's main hub, Midway Intl. Airport (MDW), is about 14 kilometers southwest of the downtown area. As well as the price of fares, consider things like transportation options from the airport and the distance to your hotel before making your decision. Get your Chicago vacation off to a terrific start by checking out Wrigley Field and Millennium Park.
Can I change the date of my flight from Logan Intl. Airport (BOS) to Midway Airport?
It's easy to make amendments to your Logan Intl. Airport to MDW trip yourself. Access your details via the Expedia Trips portal and choose "change flight." Look around for new flights and secure the one that works best with your plans. You'll see an estimate of the extra charges, if applicable. Alternatively, head to our Customer Service portal to connect with our Virtual Agent and quickly get answers to all your questions.

Travel information

Origin airport
Logan Intl.
Destination airport
Midway Intl.
Roundtrip price
AED1,350
Distance
1371 km
Average flight time
2 hours 41 mins

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Chicago nearby Airports

Chicago