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Cheap flights from Boston to Chicago from $37

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Boston to Chicago departing on 8/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Cheap round-trip flights

Southwest Logo
6:30 pm - 8:15 pmBOS-MDW
2h 45mnonstop
Southwest Logo
6:45 pm - 10:05 pmMDW-BOS
2h 20mnonstop
$79Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
6:45 am - 10:00 amMDW-BOS
2h 15mnonstop
$84Southwest
Find Deal
Thu, Aug 21 - Mon, Aug 25
Southwest Logo
10:45 am - 2:50 pmBOS-MDW
5h 05m1 stop
Southwest Logo
6:45 pm - 10:05 pmMDW-BOS
2h 20mnonstop
$89Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
2:35 pm - 11:00 pmMDW-BOS
7h 25m1 stop
$94Southwest
Find Deal
Thu, Aug 21 - Mon, Aug 25
Southwest Logo
5:30 am - 7:05 amBOS-MDW
2h 35mnonstop
Southwest Logo
9:55 am - 1:20 pmMDW-BOS
2h 25mnonstop
$95Southwest
Find Deal
Sun, Sep 7 - Wed, Sep 10
Southwest Logo
5:50 am - 7:25 amBOS-MDW
2h 35mnonstop
Southwest Logo
6:10 pm - 9:35 pmMDW-BOS
2h 25mnonstop
$96Southwest
Find Deal
Sat, Aug 30 - Tue, Sep 2
Southwest Logo
10:45 am - 2:50 pmBOS-MDW
5h 05m1 stop
Southwest Logo
2:35 pm - 11:00 pmMDW-BOS
7h 25m1 stop
$98Southwest
Find Deal
Thu, Sep 4 - Mon, Sep 8
Southwest Logo
3:15 pm - 4:50 pmBOS-MDW
2h 35mnonstop
Southwest Logo
8:35 am - 5:20 pmMDW-BOS
7h 45m2 stops
$99Southwest
Find Deal
Wed, Sep 24 - Tue, Sep 30
Southwest Logo
5:15 am - 6:45 amBOS-MDW
2h 30mnonstop
Southwest Logo
7:30 am - 6:10 pmMDW-BOS
9h 40m1 stop
$100Southwest
Find Deal
Thu, Sep 18 - Mon, Sep 22
Southwest Logo
10:50 am - 4:25 pmBOS-MDW
6h 35m1 stop
Southwest Logo
11:45 am - 5:05 pmMDW-BOS
4h 20m1 stop
$103Southwest
Find Deal
Tue, Aug 12 - Tue, Aug 19

Southwest flights from Boston to Chicago Midway Airport

Our best Southwest deals on Boston to Chicago Midway Airport flight tickets
Southwest
Sep 4
BOS6:30 pmBoston Logan Intl
2h 45m
MDW8:15 pmChicago Midway
Sep 8
MDW6:45 pmChicago Midway
2h 20m
BOS10:05 pmBoston Logan Intl
$79
Find similar
Southwest
Aug 21
BOS5:15 amBoston Logan Intl
2h 30m
MDW6:45 amChicago Midway
Aug 25
MDW6:45 amChicago Midway
2h 15m
BOS10:00 amBoston Logan Intl
$84
Find similar
Southwest
Sep 4
BOS10:45 amBoston Logan Intl
5h 05m
1 stop
MDW2:50 pmChicago Midway
Sep 8
MDW6:45 pmChicago Midway
2h 20m
BOS10:05 pmBoston Logan Intl
$89
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Frontier flights from Boston to Chicago Midway Airport

Our best Frontier deals on Boston to Chicago Midway Airport flight tickets
Frontier
Jul 20
BOS6:00 amBoston Logan Intl
17h 24m
1 stop
MDW10:24 pmChicago Midway
Jul 21
MDW6:40 pmChicago Midway
12h 19m
1 stop
BOS7:59 amBoston Logan Intl
$271
Find similar
Frontier
Jul 17
BOS6:00 amBoston Logan Intl
17h 24m
1 stop
MDW10:24 pmChicago Midway
Jul 21
MDW6:40 pmChicago Midway
12h 19m
1 stop
BOS7:59 amBoston Logan Intl
$274
Find similar
Frontier
Jul 20
BOS6:00 amBoston Logan Intl
17h 24m
1 stop
MDW10:24 pmChicago Midway
Jul 21
MDW6:40 pmChicago Midway
12h 19m
1 stop
BOS7:59 amBoston Logan Intl
$281
Find similar

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 cheapest month to fly to Chicago Midway Airport?

The month of January is, on average, the cheapest month to fly to Chicago Midway Airport from Boston, with most prices found around $200. If you are unable to visit Chicago Midway Airport during the month of January, then departing from Boston during the month September is also very affordable. Most momondo users find prices during this month for around $208.

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

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Boston. The lowest ticket price found for a Wednesday departure recently was $298. 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 $432.

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 $317 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $349. 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 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 $254 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 $185 on momondo.

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

There are 1 cabin classes available to choose from on Boston Logan Intl to Chicago Midway 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 July 2025, prices for Boston to Chicago Midway Airport flights are approximately 34% cheaper 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

$37

Fastest flight time

2h 30m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Boston in the past 72 hours is $37. The best round-trip flight deal from Boston to Chicago Midway Airport found on momondo in the last 72 hours is $79.
The fastest flight from Boston to Chicago Midway Airport takes 2h 30m
Direct flights go from Boston to Chicago Midway Airport every day.
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  • 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 30m.

  • 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
United AirlinesPriceFrom $97Free CancellationRating
7.4
8,846 reviews
Search United Airlines flights
FrontierPriceFrom $100Free CancellationRating
5.9
3,271 reviews
Search Frontier flights
SouthwestPriceFrom $125Free CancellationRating
8.0
4,250 reviews
Search Southwest flights
American AirlinesPriceFrom $187Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
DeltaPriceFrom $227Free CancellationRating
8.0
7,952 reviews
Search Delta flights

  • Southwest Flights From Boston to Chicago Midway Airport

    Southwest flies from Boston to Chicago Midway Airport around 31 times per week, with 4,249 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Boston to Chicago Midway Airport in the last 72 hours was $125 (round-trip), much lower than the average airfare cost of $253 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
Benton Harbor
Saint Joseph
Portage
Lansing
Schererville
Valparaiso
Crown Point
Munster
Monticello
Chesterton
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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