Latest deals
Insights
When to book
FAQs
Reviews
Price Alerts

Cheap flights from Boston to Chicago from $108

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
6:45 pm - 8:30 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
6:30 pm - 9:55 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 25mnonstop
$217Southwest
Thu, Sep 17 - Mon, Sep 21
Southwest Logo
10:00 pm - 11:35 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 35mnonstop
Southwest Logo
6:45 pm - 10:00 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 15mnonstop
$217Southwest
Thu, Oct 1 - Mon, Oct 5
Southwest Logo
7:05 am - 8:50 amBOS  Boston Logan Intl-MDW Chicago Midway
2h 45mnonstop
Southwest Logo
7:50 am - 11:10 amMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
$217Southwest
Thu, Nov 5 - Mon, Nov 9
Southwest Logo
4:50 pm - 6:30 pmBOS  Boston Logan Intl-MDW Chicago Midway
2h 40mnonstop
Southwest Logo
1:10 pm - 4:30 pmMDW  Chicago Midway-BOS Boston Logan Intl
2h 20mnonstop
$217Southwest
Thu, Oct 15 - Tue, Oct 20
Frontier Logo
12:15 pm - 11:47 pmBOS  Boston Logan Intl-MDW Chicago Midway
12h 32m1 stop Atlanta Hartsfield-Jackson
Frontier Logo
8:07 pm - 11:02 amMDW  Chicago Midway-BOS Boston Logan Intl
13h 55m1 stop Orlando
$246Frontier
Tue, Nov 17 - Thu, Dec 3
Frontier Logo
11:57 am - 7:02 pmBOS  Boston Logan Intl-MDW Chicago Midway
8h 05m1 stop Orlando
Frontier Logo
8:07 pm - 11:02 amMDW  Chicago Midway-BOS Boston Logan Intl
13h 55m1 stop Orlando
$247Frontier
Thu, Dec 3 - Fri, Dec 4
Frontier Logo
11:57 am - 7:02 pmBOS  Boston Logan Intl-MDW Chicago Midway
8h 05m1 stop Orlando
Frontier Logo
8:07 pm - 11:02 amMDW  Chicago Midway-BOS Boston Logan Intl
13h 55m1 stop Orlando
$247Frontier
Thu, Dec 3 - Sun, Dec 6
Delta Logo
6:05 am - 6:00 pmBOS  Boston Logan Intl-MDW Chicago Midway
12h 55m2 stops Washington, D.C. Reagan-National 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
$304Delta
Thu, Oct 22 - Tue, Oct 27
Delta Logo
6:05 am - 6:00 pmBOS  Boston Logan Intl-MDW Chicago Midway
12h 55m2 stops Washington, D.C. Reagan-National Detroit Metropolitan Wayne County
Delta Logo
6:44 pm - 11:59 pmMDW  Chicago Midway-BOS Boston Logan Intl
4h 15m1 stop Detroit Metropolitan Wayne County
$304Delta
Thu, Oct 22 - Mon, Oct 26
Delta Logo
5:27 am - 9:37 amBOS  Boston Logan Intl-MDW Chicago Midway
5h 10m1 stop Detroit Metropolitan Wayne County
Delta Logo
6:45 pm - 11:59 pmMDW  Chicago Midway-BOS Boston Logan Intl
4h 14m1 stop Detroit Metropolitan Wayne County
$314Delta
Tue, Dec 1 - Tue, Dec 1

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Southwest flights from Boston to Chicago Midway Airport

Our best Southwest deals on Boston to Chicago Midway Airport flight tickets
Southwest
Sep 17
BOS6:45 pmBoston Logan Intl
2h 45m
MDW8:30 pmChicago Midway
Sep 21
MDW6:30 pmChicago Midway
2h 25m
BOS9:55 pmBoston Logan Intl
$217
Southwest
Oct 16
BOS10:00 pmBoston Logan Intl
2h 40m
MDW11:40 pmChicago Midway
Oct 19
MDW7:50 amChicago Midway
2h 20m
BOS11:10 amBoston Logan Intl
$226
Southwest
Oct 1
BOS6:35 pmBoston Logan Intl
2h 35m
MDW8:10 pmChicago Midway
Oct 5
MDW5:50 pmChicago Midway
4h 45m
1 stop
BOS11:35 pmBoston Logan Intl
$227

Frontier flights from Boston to Chicago Midway Airport

Our best Frontier deals on Boston to Chicago Midway Airport flight tickets
Frontier
Dec 3
BOS11:57 amBoston Logan Intl
8h 05m
1 stop
MDW7:02 pmChicago Midway
Dec 6
MDW8:07 pmChicago Midway
13h 55m
1 stop
BOS11:02 amBoston Logan Intl
$254
Frontier
Dec 10
BOS11:57 amBoston Logan Intl
8h 05m
1 stop
MDW7:02 pmChicago Midway
Dec 13
MDW8:07 pmChicago Midway
13h 55m
1 stop
BOS11:02 amBoston Logan Intl
$268
Frontier
Dec 10
BOS11:57 amBoston Logan Intl
8h 05m
1 stop
MDW7:02 pmChicago Midway
Dec 13
MDW8:07 pmChicago Midway
13h 55m
1 stop
BOS11:02 amBoston Logan Intl
$273

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 9/17

6:45 pm-8:30 pm

Nonstop2h 45m

Chicago Midway

Mon 9/21

6:30 pm-9:55 pm

Nonstop2h 25m

$217
Quickest round-trip

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 10/1

10:00 pm-11:35 pm

Nonstop2h 35m

Chicago Midway

Mon 10/5

6:45 pm-10:00 pm

Nonstop2h 15m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 11/5

7:05 am-8:50 am

Nonstop2h 45m

Chicago Midway

Mon 11/9

7:50 am-11:10 am

Nonstop2h 20m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 10/15

4:50 pm-6:30 pm

Nonstop2h 40m

Chicago Midway

Tue 10/20

1:10 pm-4:30 pm

Nonstop2h 20m

$217

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 11/17

12:15 pm-11:47 pm

1 stop12h 32m

Chicago Midway

Thu 12/3

8:07 pm-11:02 am

1 stop13h 55m

$246

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 12/3

11:57 am-7:02 pm

1 stop8h 05m

Chicago Midway

Fri 12/4

8:07 pm-11:02 am

1 stop13h 55m

$247

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 12/3

11:57 am-7:02 pm

1 stop8h 05m

Chicago Midway

Sun 12/6

8:07 pm-11:02 am

1 stop13h 55m

$247

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 10/22

6:05 am-6:00 pm

2 stops12h 55m

Chicago Midway

Tue 10/27

9:29 am-4:15 pm

1 stop5h 46m

$304

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Thu 10/22

6:05 am-6:00 pm

2 stops12h 55m

Chicago Midway

Mon 10/26

6:44 pm-11:59 pm

1 stop4h 15m

$304

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 12/1

5:27 am-9:37 am

1 stop5h 10m

Chicago Midway

Tue 12/1

6:45 pm-11:59 pm

1 stop4h 14m

$314

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

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 $227 to $335.
The lowest price recently found on this route was $217.

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 $137. 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 $350. 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 in the evening is the least expensive time of day to depart. momondo users have found prices as low as $315 when looking at flights departing in the evening. 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 $278 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 August 2026, prices for Boston to Chicago Midway Airport flights are approximately 7% 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

$108

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 $108. The best round-trip flight deal from Boston to Chicago Midway Airport found on momondo in the last 72 hours is $217.
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

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
8,533 reviews
Search Delta flights
JetBluePriceFrom $117Free CancellationRating
7.1
3,034 reviews
Search JetBlue flights
SouthwestPriceFrom $137Free CancellationRating
8.0
4,195 reviews
Search Southwest flights
American AirlinesPriceFrom $181Free CancellationRating
7.1
12,019 reviews
Search American Airlines flights

  • Southwest Flights From Boston to Chicago Midway Airport

    Southwest flies from Boston to Chicago Midway Airport around 24 times per week, with 4,195 momondo users rating the airline 8.0/10. The cheapest Southwest deal from Boston to Chicago Midway Airport in the last 72 hours was $137 (round-trip), much lower than the average airfare cost of $298 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
Benton Harbor
Lansing
Saint Joseph
Valparaiso
Schererville
Munster
Chesterton
Monticello
Porter
Crown Point
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

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Wed 9/30
Wed 10/7
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Chicago