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Cheap flights from Boston to Chicago Midway Airport from $59

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 Midway Airport departing on 5/17. 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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Find the cheapest flights from Boston to Chicago

Cheap round-trip flights

KAYAK's recommended round-trip deals from the most popular airlines that fly from Boston to Chicago.
Southwest Logo
5:45 pm - 7:25 pmBOS-MDW
2h 40mnonstop
Southwest Logo
5:30 am - 8:45 amMDW-BOS
2h 15mnonstop
$117Southwest
Find Deal
Sat, May 3 - Mon, May 5
Southwest Logo
5:45 am - 7:20 amBOS-MDW
2h 35mnonstop
Southwest Logo
2:40 pm - 10:30 pmMDW-BOS
6h 50m1 stop
$127Southwest
Find Deal
Mon, May 5 - Tue, May 6
Southwest Logo
5:30 am - 1:15 pmBOS-MDW
8h 45m2 stops
Southwest Logo
7:20 pm - 10:35 pmMDW-BOS
2h 15mnonstop
$132Southwest
Find Deal
Thu, May 8 - Mon, May 12
Frontier Logo
8:00 am - 12:24 pmBOS-MDW
29h 24m1 stop
Frontier Logo
4:00 pm - 9:34 amMDW-BOS
16h 34m1 stop
$190Frontier
Find Deal
Wed, May 7 - Sun, May 11
Frontier Logo
8:00 am - 12:24 pmBOS-MDW
29h 24m1 stop
Frontier Logo
4:00 pm - 9:34 amMDW-BOS
16h 34m1 stop
$191Frontier
Find Deal
Wed, May 7 - Thu, May 8
Allegiant Air Logo
9:02 am - 7:46 pmBOS-MDW
11h 44m1 stop
Allegiant Air Logo
2:53 pm - 9:17 amMDW-BOS
17h 24m1 stop
$255Allegiant Air
Find Deal
Fri, Jun 6 - Mon, Jun 9
 Logo
9:00 am - 7:14 pmBOS-MDW
11h 14m1 stop
 Logo
8:04 pm - 11:29 pmMDW-BOS
26h 25m2 stops
Fri, May 30 - Mon, Jun 2
Delta Logo
5:10 am - 8:41 amBOS-MDW
4h 31m1 stop
Delta Logo
1:00 pm - 11:33 pmMDW-BOS
9h 33m1 stop
$295Delta
Find Deal
Thu, Jul 3 - Tue, Jul 8
Delta Logo
4:25 pm - 9:13 pmBOS-MDW
5h 48m1 stop
Delta Logo
9:16 am - 4:00 pmMDW-BOS
5h 44m1 stop
$316Delta
Find Deal
Sat, May 24 - Sun, May 25
Allegiant Air Logo
9:00 am - 7:14 pmBOS-MDW
11h 14m1 stop
Allegiant Air Logo
2:54 pm - 9:14 amMDW-BOS
17h 20m1 stop
$355Allegiant Air
Find Deal
Fri, May 23 - Mon, May 26

Frontier flights from Boston to Chicago Midway Airport

Our best Frontier deals on Boston to Chicago Midway Airport flight tickets
Frontier
May 7
BOS8:00 amBoston Logan Intl
29h 24m
1 stop
MDW12:24 pmChicago Midway
May 11
MDW4:00 pmChicago Midway
16h 34m
1 stop
BOS9:34 amBoston Logan Intl
Frontier
May 7
BOS8:00 amBoston Logan Intl
29h 24m
1 stop
MDW12:24 pmChicago Midway
May 8
MDW4:00 pmChicago Midway
16h 34m
1 stop
BOS9:34 amBoston Logan Intl
Frontier
May 5
BOS12:58 pmBoston Logan Intl
11h 49m
1 stop
MDW11:47 pmChicago Midway
May 9
MDW1:19 pmChicago Midway
10h 25m
1 stop
BOS12:44 amBoston Logan Intl

Allegiant Air flights from Boston to Chicago Midway Airport

Our best Allegiant Air deals on Boston to Chicago Midway Airport flight tickets
Allegiant Air
Jun 6
BOS9:02 amBoston Logan Intl
11h 44m
1 stop
MDW7:46 pmChicago Midway
Jun 9
MDW2:53 pmChicago Midway
17h 24m
1 stop
BOS9:17 amBoston Logan Intl
Allegiant Air
May 23
BOS9:00 amBoston Logan Intl
11h 14m
1 stop
MDW7:14 pmChicago Midway
May 26
MDW2:54 pmChicago Midway
17h 20m
1 stop
BOS9:14 amBoston Logan Intl
Allegiant Air
May 23
BOS9:00 amBoston Logan Intl
11h 14m
1 stop
MDW7:14 pmChicago Midway
May 26
MDW2:54 pmChicago Midway
17h 20m
1 stop
BOS9:14 amBoston Logan Intl

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, Thursday is the cheapest day to fly to Chicago Midway Airport from Boston. The lowest ticket price found for a Thursday departure recently was $324. 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 $461.

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 $347 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $371. 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 7 weeks ahead of your departure date. In general, you can expect to find flights to Chicago Midway Airport for around $268 when searching 7 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 $188 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 April 2025, prices for Boston to Chicago Midway Airport flights are approximately 44% 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

$59

Fastest flight time

2h 35m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Boston in the past 72 hours is $59. The best round-trip flight deal from Boston to Chicago Midway Airport found on momondo in the last 72 hours is $117.
The fastest flight from Boston to Chicago Midway Airport takes 2h 35m
Direct flights go from Boston to Chicago Midway Airport every day.

  • 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
Spirit AirlinesPriceFrom $76Free CancellationRating
6.3
7,926 reviews
Search Spirit Airlines flights
United AirlinesPriceFrom $97Free CancellationRating
7.4
8,667 reviews
Search United Airlines flights
FrontierPriceFrom $100Free CancellationRating
6.0
3,281 reviews
Search Frontier flights
SouthwestPriceFrom $141Free CancellationRating
8.0
4,280 reviews
Search Southwest flights
DeltaPriceFrom $237Free CancellationRating
8.0
7,916 reviews
Search Delta flights
  • Southwest Flights From Boston to Chicago Midway Airport

    Southwest flies from Boston to Chicago Midway Airport around 15 times per week, with 4,280 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Boston to Chicago Midway Airport in the last 72 hours was $141 (round-trip), much lower than the average airfare cost of $257 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
Portage
Lansing
Saint Joseph
Schererville
Valparaiso
Munster
Crown Point
Monticello
Chesterton
Griffith
Porter
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.


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