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Cheap flights from Boston to Chicago from $64

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 11/4. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Cheap round-trip flights

Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
Southwest Logo
7:15 pm - 10:30 pmMDW-BOS
2h 15mnonstop
$123Southwest
Find Deal
Tue, Nov 11 - Fri, Nov 14
Southwest Logo
5:35 am - 10:15 amBOS-MDW
5h 40m1 stop
Southwest Logo
6:05 am - 9:20 amMDW-BOS
2h 15mnonstop
$127Southwest
Find Deal
Thu, Oct 2 - Sun, Oct 5
Southwest Logo
5:35 am - 1:20 pmBOS-MDW
8h 45m2 stops
Southwest Logo
6:05 am - 9:20 amMDW-BOS
2h 15mnonstop
$132Southwest
Find Deal
Thu, Oct 2 - Sun, Oct 5
Southwest Logo
5:00 am - 6:40 amBOS-MDW
2h 40mnonstop
Southwest Logo
5:45 am - 5:10 pmMDW-BOS
10h 25m1 stop
$133Southwest
Find Deal
Fri, Oct 31 - Sun, Nov 2
Southwest Logo
6:50 pm - 11:30 pmBOS-MDW
5h 40m1 stop
Southwest Logo
5:00 am - 12:50 pmMDW-BOS
6h 50m1 stop
$137Southwest
Find Deal
Fri, Nov 14 - Sun, Nov 16
Southwest Logo
5:35 pm - 9:05 pmBOS-MDW
4h 30m1 stop
Southwest Logo
9:30 am - 6:15 pmMDW-BOS
7h 45m2 stops
$138Southwest
Find Deal
Tue, Nov 4 - Fri, Nov 7
Frontier Logo
11:44 am - 9:33 amBOS-MDW
22h 49m1 stop
Frontier Logo
12:09 pm - 8:33 amMDW-BOS
19h 24m1 stop
$154Frontier
Find Deal
Thu, Oct 16 - Sun, Oct 19
Frontier Logo
9:18 am - 4:20 pmBOS-MDW
8h 02m1 stop
Frontier Logo
9:26 pm - 8:55 amMDW-BOS
10h 29m1 stop
$155Frontier
Find Deal
Fri, Oct 24 - Sun, Oct 26
Frontier Logo
11:44 am - 9:33 amBOS-MDW
22h 49m1 stop
Frontier Logo
10:49 am - 8:33 amMDW-BOS
20h 44m1 stop
$156Frontier
Find Deal
Thu, Oct 16 - Thu, Oct 23
Multiple Airlines Logo
9:39 am - 2:33 pmBOS-MDW
5h 54m1 stop
Multiple Airlines Logo
1:37 pm - 11:16 amMDW-BOS
20h 39m2 stops
$201Multiple Airlines
Find Deal
Thu, Oct 30 - Mon, Nov 3

Frontier flights from Boston to Chicago Midway Airport

Our best Frontier deals on Boston to Chicago Midway Airport flight tickets
Frontier
Oct 16
BOS11:44 amBoston Logan Intl
22h 49m
1 stop
MDW9:33 amChicago Midway
Oct 19
MDW12:09 pmChicago Midway
19h 24m
1 stop
BOS8:33 amBoston Logan Intl
$154
Find similar
Frontier
Oct 24
BOS9:18 amBoston Logan Intl
8h 02m
1 stop
MDW4:20 pmChicago Midway
Oct 26
MDW9:26 pmChicago Midway
10h 29m
1 stop
BOS8:55 amBoston Logan Intl
$155
Find similar
Frontier
Oct 16
BOS11:44 amBoston Logan Intl
22h 49m
1 stop
MDW9:33 amChicago Midway
Oct 23
MDW10:49 amChicago Midway
20h 44m
1 stop
BOS8:33 amBoston Logan Intl
$156
Find similar

Southwest flights from Boston to Chicago Midway Airport

Our best Southwest deals on Boston to Chicago Midway Airport flight tickets
Southwest
Nov 11
BOS5:35 pmBoston Logan Intl
4h 30m
1 stop
MDW9:05 pmChicago Midway
Nov 14
MDW7:15 pmChicago Midway
2h 15m
BOS10:30 pmBoston Logan Intl
$123
Find similar
Southwest
Oct 1
BOS2:50 pmBoston Logan Intl
6h 35m
1 stop
MDW8:25 pmChicago Midway
Oct 4
MDW6:30 amChicago Midway
2h 15m
BOS9:45 amBoston Logan Intl
$127
Find similar
Southwest
Oct 2
BOS5:35 amBoston Logan Intl
8h 45m
2 stops
MDW1:20 pmChicago Midway
Oct 5
MDW6:05 amChicago Midway
2h 15m
BOS9:20 amBoston Logan Intl
$132
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Boston to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated September 17, 2025.
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

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 11/11

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

Fri 11/14

7:15 pm-10:30 pm

Nonstop2h 15m

$123

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/2

5:35 am-10:15 am

1 stop5h 40m

Chicago Midway

Sun 10/5

6:05 am-9:20 am

Nonstop2h 15m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/2

5:35 am-1:20 pm

2 stops8h 45m

Chicago Midway

Sun 10/5

6:05 am-9:20 am

Nonstop2h 15m

$132

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/31

5:00 am-6:40 am

Nonstop2h 40m

Chicago Midway

Sun 11/2

5:45 am-5:10 pm

1 stop10h 25m

$133

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 11/14

6:50 pm-11:30 pm

1 stop5h 40m

Chicago Midway

Sun 11/16

5:00 am-12:50 pm

1 stop6h 50m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 11/4

5:35 pm-9:05 pm

1 stop4h 30m

Chicago Midway

Fri 11/7

9:30 am-6:15 pm

2 stops7h 45m

$138

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/16

11:44 am-9:33 am

1 stop22h 49m

Chicago Midway

Sun 10/19

12:09 pm-8:33 am

1 stop19h 24m

$154

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 10/24

9:18 am-4:20 pm

1 stop8h 02m

Chicago Midway

Sun 10/26

9:26 pm-8:55 am

1 stop10h 29m

$155

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/16

11:44 am-9:33 am

1 stop22h 49m

Chicago Midway

Thu 10/23

10:49 am-8:33 am

1 stop20h 44m

$156

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 10/30

9:39 am-2:33 pm

1 stop5h 54m

Chicago Midway

Mon 11/3

1:37 pm-11:16 am

2 stops20h 39m

$201

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 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 June is also very affordable. Most momondo users find prices during this month for around $217.

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 $300. 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 $424.

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 $325 when looking at flights departing at noon. Try not to purchase tickets in the morning because they tend to be around $347. 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 $255 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 $164 on momondo.

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

There is only 1 cabin class 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 September 2025, prices for Boston to Chicago Midway Airport flights are approximately 28% 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

$171

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 $171. The best round-trip flight deal from Boston to Chicago Midway Airport found on momondo in the last 72 hours is $210.
The fastest flight from Boston to Chicago Midway Airport takes 2h 35m
Direct flights go from Boston to Chicago Midway Airport every day.
Search flight deals

  • 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
United AirlinesPriceFrom $97Free CancellationRating
7.4
8,926 reviews
Search United Airlines flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,173 reviews
Search Frontier flights
SouthwestPriceFrom $120Free CancellationRating
8.0
4,242 reviews
Search Southwest flights
DeltaPriceFrom $227Free CancellationRating
7.9
7,961 reviews
Search Delta flights

  • Southwest Flights From Boston to Chicago Midway Airport

    Southwest flies from Boston to Chicago Midway Airport around 21 times per week, with 4,242 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Boston to Chicago Midway Airport in the last 72 hours was $120 (round-trip), much lower than the average airfare cost of $268 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
Lansing
Portage
Schererville
Valparaiso
Crown Point
Munster
Chesterton
Monticello
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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