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Cheap flights from Boston to Chicago from $111

1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Boston to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Southwest Logo
5:55 pm - 7:40 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
8:30 am - 12:00 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 30mnonstop
$214Southwest
Thu, Dec 3 - Mon, Dec 7
Southwest Logo
3:10 pm - 4:55 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
1:15 pm - 4:20 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 05mnonstop
$214Southwest
Sat, Dec 5 - Tue, Dec 8
Southwest Logo
10:25 pm - 12:25 amBOS  Boston Logan Intl-MDW Chicago Midway
3h 00mnonstop
Southwest Logo
6:25 pm - 9:45 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
$214Southwest
Mon, Nov 30 - Thu, Dec 3
Southwest Logo
3:10 pm - 4:55 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
1:15 pm - 4:20 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 05mnonstop
$214Southwest
Sat, Dec 5 - Mon, Dec 7
Frontier Logo
11:27 am - 5:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 20m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:42 pm - 10:11 amMDW  Chicago Midway-BOS Boston Logan Intl
12h 29m1 stop Orlando
$220Frontier
Sat, Nov 14 - Sat, Nov 21
Frontier Logo
12:39 pm - 11:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
12h 08m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:42 pm - 10:11 amMDW  Chicago Midway-BOS Boston Logan Intl
12h 29m1 stop Orlando
$220Frontier
Wed, Nov 18 - Tue, Nov 24
Frontier Logo
11:27 am - 5:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
7h 20m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:42 pm - 10:11 amMDW  Chicago Midway-BOS Boston Logan Intl
12h 29m1 stop Orlando
$220Frontier
Sat, Nov 14 - Tue, Nov 24
Delta Logo
5:39 am - 9:32 amBOS  Boston Logan Intl-MDW Chicago Midway
4h 53m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:29 am - 4:15 pmMDW  Chicago Midway-BOS Boston Logan Intl
5h 46m1 stop Detroit Metropolitan Wayne County
$317Delta
Mon, Nov 2 - Fri, Nov 6
Delta Logo
5:30 am - 9:46 amBOS  Boston Logan Intl-MDW Chicago Midway
5h 16m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:30 am - 3:52 pmMDW  Chicago Midway-BOS Boston Logan Intl
5h 22m1 stop Detroit Metropolitan Wayne County
$317Delta
Fri, Nov 13 - Wed, Nov 18
Delta Logo
9:05 am - 1:01 pmBOS  Boston Logan Intl-MDW Chicago Midway
4h 56m1 stop Detroit Metropolitan Wayne County
Delta Logo
9:37 am - 3:54 pmMDW  Chicago Midway-BOS Boston Logan Intl
5h 17m1 stop Detroit Metropolitan Wayne County
$317Delta
Fri, Dec 4 - Mon, Dec 7

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Southwest flights from Boston to Chicago Midway Airport

Our best Southwest deals on Boston to Chicago Midway Airport flight tickets
Southwest
Dec 3
BOS5:55 pmBoston Logan Intl
2h 45m
MDW7:40 pmChicago Midway
Dec 7
MDW8:30 amChicago Midway
2h 30m
BOS12:00 pmBoston Logan Intl
$214
Southwest
Nov 10
BOS1:20 pmBoston Logan Intl
7h 30m
2 stops
MDW7:50 pmChicago Midway
Nov 11
MDW8:30 amChicago Midway
2h 30m
BOS12:00 pmBoston Logan Intl
$216
Southwest
Nov 10
BOS5:20 amBoston Logan Intl
7h 45m
1 stop
MDW12:05 pmChicago Midway
Nov 10
MDW3:50 pmChicago Midway
4h 55m
1 stop
BOS9:45 pmBoston Logan Intl
$221

Frontier flights from Boston to Chicago Midway Airport

Our best Frontier deals on Boston to Chicago Midway Airport flight tickets
Frontier
Nov 14
BOS11:27 amBoston Logan Intl
7h 20m
1 stop
MDW5:47 pmChicago Midway
Nov 24
MDW8:42 pmChicago Midway
12h 29m
1 stop
BOS10:11 amBoston Logan Intl
$220
Frontier
Nov 18
BOS12:39 pmBoston Logan Intl
12h 08m
1 stop
MDW11:47 pmChicago Midway
Nov 22
MDW8:42 pmChicago Midway
12h 29m
1 stop
BOS10:11 amBoston Logan Intl
$228
Frontier
Nov 14
BOS11:27 amBoston Logan Intl
7h 20m
1 stop
MDW5:47 pmChicago Midway
Nov 22
MDW8:42 pmChicago Midway
12h 29m
1 stop
BOS10:11 amBoston Logan Intl
$230

momondo Fare Finder

 
Use the filters below to find and compare flights from Boston to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 12/3

5:55 pm-7:40 pm

Nonstop2h 45m

Chicago Midway

Mon 12/7

8:30 am-12:00 pm

Nonstop2h 30m

$214
Quickest round-trip

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 12/5

3:10 pm-4:55 pm

Nonstop2h 45m

Chicago Midway

Tue 12/8

1:15 pm-4:20 pm

Nonstop2h 05m

$214

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Mon 11/30

10:25 pm-12:25 am

Nonstop3h 00m

Chicago Midway

Thu 12/3

6:25 pm-9:45 pm

Nonstop2h 20m

$214

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 12/5

3:10 pm-4:55 pm

Nonstop2h 45m

Chicago Midway

Mon 12/7

1:15 pm-4:20 pm

Nonstop2h 05m

$214

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 11/14

11:27 am-5:47 pm

1 stop7h 20m

Chicago Midway

Sat 11/21

8:42 pm-10:11 am

1 stop12h 29m

$220

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Wed 11/18

12:39 pm-11:47 pm

1 stop12h 08m

Chicago Midway

Tue 11/24

8:42 pm-10:11 am

1 stop12h 29m

$220

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 11/14

11:27 am-5:47 pm

1 stop7h 20m

Chicago Midway

Tue 11/24

8:42 pm-10:11 am

1 stop12h 29m

$220

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Mon 11/2

5:39 am-9:32 am

1 stop4h 53m

Chicago Midway

Fri 11/6

9:29 am-4:15 pm

1 stop5h 46m

$317

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Fri 11/13

5:30 am-9:46 am

1 stop5h 16m

Chicago Midway

Wed 11/18

9:30 am-3:52 pm

1 stop5h 22m

$317

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Fri 12/4

9:05 am-1:01 pm

1 stop4h 56m

Chicago Midway

Mon 12/7

9:37 am-3:54 pm

1 stop5h 17m

$317

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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See travel insights to Chicago from

How to get the cheapest flight ticket from Boston to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the typical price of a round-trip flight between Boston and Chicago Midway Airport?

Prices are currently low for flights on this route.

Typical prices usually range from $283 to $426.
The lowest price recently found on this route was $214.

What is the cheapest month to fly to Chicago Midway Airport?

The month of December is, on average, the cheapest month to fly to Chicago Midway Airport from Boston, with most prices found around $134. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Boston during the month January is also very affordable. Most momondo users find prices during this month for around $162.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Thursday is the cheapest day to fly to Chicago Midway Airport from Boston. The lowest ticket price found for a Thursday departure recently was $358. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Boston because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $455.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Boston at noon is the least expensive time of day to depart. momondo users have found prices as low as $343 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $399. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Boston Logan Intl to Chicago Midway flight route?

Fly from Boston Logan Intl to Chicago Midway for the best Boston Logan Intl - Chicago Midway flight prices

How far in advance should I book a flight from Boston to Chicago Midway Airport?

You are more likely to see cheaper flights to Chicago Midway Airport from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $281 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago Midway Airport from Boston for as low as $238 on momondo.

What cabin class options are available on Boston to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Boston to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

How have Boston to Chicago Midway Airport flight prices changed over time?

As of October 2026, prices for Boston to Chicago Midway Airport flights are approximately 71% more expensive when compared to flights at the same time last year.

When to book flights from Boston to Chicago Midway Airport

Are you open to changing your travel dates? Check out the ideal times to fly from Boston to Chicago Midway Airport according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Boston to Chicago Midway Airport (BOS to MDW) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago Midway Airport

Best Price Found

$111

Fastest flight time

2h 35m

Direct flights

Mon, Tue, Wed, Fri, Sat and Sun
The best one-way flight to Chicago Midway Airport from Boston in the past 72 hours is $111. The best round-trip flight deal from Boston to Chicago Midway Airport found on momondo in the last 72 hours is $214.
The fastest flight from Boston to Chicago Midway Airport takes 2h 35m
Direct flights go from Boston to Chicago Midway Airport on Monday, Tuesday, Wednesday, Friday, Saturday and Sunday. The only airline offering direct flights is Southwest.
Search flight deals

Frequently asked questions about flying from Boston to Chicago Midway Airport

  • How far is Boston Logan Intl to Chicago Midway by plane?

    The distance between Boston Logan Intl and Chicago Midway is about 854.8 mi. A reasonable flight in good conditions will take 2h 35m.

  • When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago Midway Airport?

    Prices for flights from Boston Logan Intl Airport to Chicago Midway Airport were last updated today.

  • How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago Midway Airport?

  • How old do you have to be to fly from Boston Logan Intl Airport to Chicago Midway Airport?

    The minimum age for a child to fly alone is five, but airlines that offer an unaccompanied minor (UNMR) service may have their own age limitations. Flight duration, scheduling, and layovers are among the considerations that may influence age limits. We recommend that you double-check with the airline you are booking with for travel from Boston Logan Intl Airport to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents you'll need for your trip to Chicago Midway Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Chicago Midway Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Boston to Chicago Midway Airport?

  • What is the most popular airline from Boston to Chicago Midway Airport?

Best airlines flying from Boston to Chicago Midway Airport

Compare and see reviews for airlines that fly from Boston to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
DeltaPriceFrom $88Free CancellationRating
7.8
8,651 reviews
Search Delta flights
SouthwestPriceFrom $147Free CancellationRating
7.9
4,212 reviews
Search Southwest flights
JetBluePriceFrom $150Free CancellationRating
7.1
3,058 reviews
Search JetBlue flights
American AirlinesPriceFrom $181Free CancellationRating
7.0
12,178 reviews
Search American Airlines flights

  • Southwest Flights From Boston to Chicago Midway Airport

    Southwest flies from Boston to Chicago Midway Airport around 27 times per week, with 4,212 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Boston to Chicago Midway Airport in the last 72 hours was $147 (round-trip), much lower than the average airfare cost of $311 for Southwest flights on this route.

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
Merrillville
New Buffalo
Hammond
Portage
Saint Joseph
Benton Harbor
Lansing
Valparaiso
Schererville
Munster
Chesterton
Monticello
Crown Point
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Boston to Chicago?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Chicago from Boston.

Can I find flights from Boston to Chicago with flexible booking policies on momondo?

Yes. momondo enables you to select and highlight flights to Chicago from Boston with this policy.

How can momondo help me find flights from Boston to Chicago?

Once you have performed a search for Boston to Chicago flights, momondo helps you find the right one by offering useful filters to narrow down your flight selection. Flights can be filtered by multiple factors such as airline, airport and price; but also by other criteria like aircraft type and payment method.

I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Chicago from Boston. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.

An easier way to manage your Chicago Midway Airport trip

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