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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 1/28. 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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0 bags

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Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
2:00 pm - 5:10 pm
MDW
-
BOS
2h 10mnonstop
$127Southwest
Sun, Jan 18 - Tue, Jan 20
Frontier Logo
6:00 am - 11:45 am
BOS
-
MDW
6h 45m1 stop
Frontier Logo
5:01 pm - 1:13 am
MDW
-
BOS
7h 12m1 stop
$128Frontier
Thu, Jan 22 - Sun, Jan 25
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
Frontier Logo
1:20 pm - 1:03 am
MDW
-
BOS
10h 43m1 stop
$130Frontier
Wed, Jan 28 - Wed, Feb 4
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
2:00 pm - 5:10 pm
MDW
-
BOS
2h 10mnonstop
$137Southwest
Tue, Jan 6 - Fri, Jan 9
Southwest Logo
5:30 am - 7:15 am
BOS
-
MDW
2h 45mnonstop
Southwest Logo
5:15 pm - 10:55 pm
MDW
-
BOS
4h 40m1 stop
$142Southwest
Thu, Jan 1 - Mon, Jan 5
Multiple Airlines Logo
3:43 pm - 11:09 pm
BOS
-
MDW
8h 26m1 stop
Multiple Airlines Logo
3:01 pm - 4:19 pm
MDW
-
BOS
24h 18m1 stop
$143Multiple Airlines
Fri, Jan 9 - Mon, Jan 12
Frontier Logo
6:00 am - 12:05 pm
BOS
-
MDW
7h 05m1 stop
Frontier Logo
5:01 pm - 1:13 am
MDW
-
BOS
7h 12m1 stop
$145Frontier
Wed, Jan 21 - Mon, Jan 26
Southwest Logo
2:40 pm - 4:30 pm
BOS
-
MDW
2h 50mnonstop
Southwest Logo
2:00 pm - 5:10 pm
MDW
-
BOS
2h 10mnonstop
$147Southwest
Wed, Jan 7 - Thu, Jan 8
Multiple Airlines Logo
3:43 pm - 11:09 pm
BOS
-
MDW
8h 26m1 stop
Multiple Airlines Logo
7:20 pm - 4:19 pm
MDW
-
BOS
19h 59m1 stop
$150Multiple Airlines
Mon, Jan 12 - Mon, Jan 19
Southwest Logo
5:30 am - 7:20 am
BOS
-
MDW
2h 50mnonstop
Southwest Logo
2:35 pm - 9:45 pm
MDW
-
BOS
6h 10m1 stop
$152Southwest
Tue, Jan 6 - Fri, Jan 9

Southwest flights from Boston to Chicago Midway Airport

Our best Southwest deals on Boston to Chicago Midway Airport flight tickets
Southwest
Jan 18
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
Jan 20
MDW2:00 pmChicago Midway
2h 10m
BOS5:10 pmBoston Logan Intl
$127
Find similar
Southwest
Jan 6
BOS5:30 amBoston Logan Intl
2h 50m
MDW7:20 amChicago Midway
Jan 9
MDW2:00 pmChicago Midway
2h 10m
BOS5:10 pmBoston Logan Intl
$137
Find similar
Southwest
Jan 1
BOS5:30 amBoston Logan Intl
2h 45m
MDW7:15 amChicago Midway
Jan 5
MDW5:15 pmChicago Midway
4h 40m
1 stop
BOS10:55 pmBoston Logan Intl
$142
Find similar

Frontier flights from Boston to Chicago Midway Airport

Our best Frontier deals on Boston to Chicago Midway Airport flight tickets
Frontier
Jan 22
BOS6:00 amBoston Logan Intl
6h 45m
1 stop
MDW11:45 amChicago Midway
Jan 25
MDW5:01 pmChicago Midway
7h 12m
1 stop
BOS1:13 amBoston Logan Intl
$128
Find similar
Frontier
Jan 28
BOS6:00 amBoston Logan Intl
7h 05m
1 stop
MDW12:05 pmChicago Midway
Feb 4
MDW1:20 pmChicago Midway
10h 43m
1 stop
BOS1:03 amBoston Logan Intl
$130
Find similar
Frontier
Jan 21
BOS6:00 amBoston Logan Intl
7h 05m
1 stop
MDW12:05 pmChicago Midway
Jan 26
MDW5:01 pmChicago Midway
7h 12m
1 stop
BOS1:13 amBoston Logan Intl
$145
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 December 15, 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

Sun 1/18

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Tue 1/20

2:00 pm-5:10 pm

Nonstop2h 10m

$127

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/22

6:00 am-11:45 am

1 stop6h 45m

Chicago Midway

Sun 1/25

5:01 pm-1:13 am

1 stop7h 12m

$128

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/28

6:00 am-12:05 pm

1 stop7h 05m

Chicago Midway

Wed 2/4

1:20 pm-1:03 am

1 stop10h 43m

$130

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 1/6

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Fri 1/9

2:00 pm-5:10 pm

Nonstop2h 10m

$137

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 1/1

5:30 am-7:15 am

Nonstop2h 45m

Chicago Midway

Mon 1/5

5:15 pm-10:55 pm

1 stop4h 40m

$142

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Fri 1/9

3:43 pm-11:09 pm

1 stop8h 26m

Chicago Midway

Mon 1/12

3:01 pm-4:19 pm

1 stop24h 18m

$143

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/21

6:00 am-12:05 pm

1 stop7h 05m

Chicago Midway

Mon 1/26

5:01 pm-1:13 am

1 stop7h 12m

$145

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Wed 1/7

2:40 pm-4:30 pm

Nonstop2h 50m

Chicago Midway

Thu 1/8

2:00 pm-5:10 pm

Nonstop2h 10m

$147

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Mon 1/12

3:43 pm-11:09 pm

1 stop8h 26m

Chicago Midway

Mon 1/19

7:20 pm-4:19 pm

1 stop19h 59m

$150

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Tue 1/6

5:30 am-7:20 am

Nonstop2h 50m

Chicago Midway

Fri 1/9

2:35 pm-9:45 pm

1 stop6h 10m

$152

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 December is, on average, the cheapest month to fly to Chicago Midway Airport from Boston, with most prices found around $177. If you are unable to visit Chicago Midway Airport during the month of December, then departing from Boston during the month September is also very affordable. Most momondo users find prices during this month for around $213.

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 $281. 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 $413.

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

Flying to Chicago Midway Airport from Boston in the evening is the least expensive time of day to depart. momondo users have found prices as low as $269 when looking at flights departing in the evening. Try not to purchase tickets in the afternoon because they tend to be around $344. 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 $259 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 December 2025, prices for Boston to Chicago Midway Airport flights are approximately 44% 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

$166

Fastest flight time

2h 40m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Boston in the past 72 hours is $166. The best round-trip flight deal from Boston to Chicago Midway Airport found on momondo in the last 72 hours is $289.
The fastest flight from Boston to Chicago Midway Airport takes 2h 40m
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 40m.

  • 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
SouthwestPriceFrom $117Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
DeltaPriceFrom $207Free CancellationRating
7.9
8,008 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 4,250 momondo users rating the airline 7.9/10. The cheapest Southwest deal from Boston to Chicago Midway Airport in the last 72 hours was $117 (round-trip), much lower than the average airfare cost of $271 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
Valparaiso
Schererville
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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