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Cheap flights from Boston to Chicago from $34

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 8/28. 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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Cheap round-trip flights

Southwest Logo
8:20 pm - 9:55 pmBOS-MDW
2h 35mnonstop
Southwest Logo
4:45 pm - 8:05 pmMDW-BOS
2h 20mnonstop
$67Southwest
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Thu, Sep 4 - Mon, Sep 8
Southwest Logo
9:10 am - 10:50 amBOS-MDW
2h 40mnonstop
Southwest Logo
2:35 pm - 11:00 pmMDW-BOS
7h 25m1 stop
$77Southwest
Find Deal
Sat, Sep 6 - Mon, Sep 8
JetBlue Logo
7:00 am - 8:56 amBOS-ORD
2h 56mnonstop
JetBlue Logo
7:50 pm - 11:25 pmORD-BOS
2h 35mnonstop
$85JetBlue
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Thu, Sep 4 - Mon, Sep 8
JetBlue Logo
4:05 pm - 5:55 pmBOS-ORD
2h 50mnonstop
JetBlue Logo
8:00 pm - 11:16 pmORD-BOS
2h 16mnonstop
$88JetBlue
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Fri, Oct 24 - Mon, Oct 27
American Airlines Logo
11:00 am - 1:00 pmBOS-ORD
3h 00mnonstop
American Airlines Logo
7:10 pm - 10:40 pmORD-BOS
2h 30mnonstop
$94American Airlines
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Thu, Sep 4 - Mon, Sep 8
American Airlines Logo
7:19 pm - 9:25 pmBOS-ORD
3h 06mnonstop
American Airlines Logo
3:08 pm - 6:29 pmORD-BOS
2h 21mnonstop
$98American Airlines
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Fri, Nov 14 - Mon, Nov 17
United Airlines Logo
6:16 pm - 8:10 pmBOS-ORD
2h 54mnonstop
United Airlines Logo
7:30 am - 11:01 amORD-BOS
2h 31mnonstop
$99United Airlines
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Fri, Sep 5 - Sun, Sep 7
Delta Logo
5:00 pm - 7:11 pmBOS-ORD
3h 11mnonstop
Delta Logo
6:00 pm - 9:38 pmORD-BOS
2h 38mnonstop
$117Delta
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Sat, Aug 30 - Wed, Sep 3
United Airlines Logo
6:16 pm - 8:10 pmBOS-ORD
2h 54mnonstop
United Airlines Logo
2:15 pm - 5:46 pmORD-BOS
2h 31mnonstop
$129United Airlines
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Thu, Aug 28 - Sun, Aug 31
Delta Logo
11:00 am - 6:02 pmBOS-ORD
8h 02m1 stop
Delta Logo
7:00 am - 10:30 amORD-BOS
2h 30mnonstop
$130Delta
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Thu, Sep 4 - Mon, Sep 8

United Airlines flights from Boston to Chicago

Our best United Airlines deals on Boston to Chicago flight tickets
United Airlines
Sep 5
BOS6:16 pmBoston Logan Intl
2h 54m
ORD8:10 pmChicago O'Hare Intl
Sep 7
ORD7:30 amChicago O'Hare Intl
2h 31m
BOS11:01 amBoston Logan Intl
$99
Find similar
United Airlines
Aug 14
BOS8:20 pmBoston Logan Intl
2h 52m
ORD10:12 pmChicago O'Hare Intl
Aug 21
ORD6:30 amChicago O'Hare Intl
2h 26m
BOS9:56 amBoston Logan Intl
$108
Find similar
United Airlines
Aug 15
BOS8:20 pmBoston Logan Intl
2h 52m
ORD10:12 pmChicago O'Hare Intl
Sep 16
ORD7:30 amChicago O'Hare Intl
2h 31m
BOS11:01 amBoston Logan Intl
$118
Find similar

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets
Delta
Aug 30
BOS5:00 pmBoston Logan Intl
3h 11m
ORD7:11 pmChicago O'Hare Intl
Sep 3
ORD6:00 pmChicago O'Hare Intl
2h 38m
BOS9:38 pmBoston Logan Intl
$117
Find similar
Delta
Sep 4
BOS11:00 amBoston Logan Intl
8h 02m
1 stop
ORD6:02 pmChicago O'Hare Intl
Sep 8
ORD7:00 amChicago O'Hare Intl
2h 30m
BOS10:30 amBoston Logan Intl
$130
Find similar
Delta
Sep 16
BOS11:55 amBoston Logan Intl
2h 48m
ORD1:43 pmChicago O'Hare Intl
Sep 27
ORD7:25 amChicago O'Hare Intl
2h 30m
BOS10:55 amBoston Logan Intl
$137
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momondo Fare Finder

 
Customize your flight search to find flights from Boston to Chicago 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 August 5, 2025.
Use the filters below to find and compare flights from Boston to Chicago that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Thu 9/4

8:20 pm-9:55 pm

Nonstop2h 35m

Chicago Midway

Mon 9/8

4:45 pm-8:05 pm

Nonstop2h 20m

$67

BostonChicago

BOS - MDW

BOSMDW

Boston Logan Intl

Sat 9/6

9:10 am-10:50 am

Nonstop2h 40m

Chicago Midway

Mon 9/8

2:35 pm-11:00 pm

1 stop7h 25m

$77

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

7:00 am-8:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Mon 9/8

7:50 pm-11:25 pm

Nonstop2h 35m

$85

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 10/24

4:05 pm-5:55 pm

Nonstop2h 50m

Chicago O'Hare Intl

Mon 10/27

8:00 pm-11:16 pm

Nonstop2h 16m

$88

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

11:00 am-1:00 pm

Nonstop3h 00m

Chicago O'Hare Intl

Mon 9/8

7:10 pm-10:40 pm

Nonstop2h 30m

$94

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 11/14

7:19 pm-9:25 pm

Nonstop3h 06m

Chicago O'Hare Intl

Mon 11/17

3:08 pm-6:29 pm

Nonstop2h 21m

$98

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/5

6:16 pm-8:10 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sun 9/7

7:30 am-11:01 am

Nonstop2h 31m

$99

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/30

5:00 pm-7:11 pm

Nonstop3h 11m

Chicago O'Hare Intl

Wed 9/3

6:00 pm-9:38 pm

Nonstop2h 38m

$117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 8/28

6:16 pm-8:10 pm

Nonstop2h 54m

Chicago O'Hare Intl

Sun 8/31

2:15 pm-5:46 pm

Nonstop2h 31m

$129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/4

11:00 am-6:02 pm

1 stop8h 02m

Chicago O'Hare Intl

Mon 9/8

7:00 am-10:30 am

Nonstop2h 30m

$130

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

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?

The month of September is, on average, the cheapest month to fly to Chicago from Boston, with most prices found around $177. If you’re not able to fly to Chicago in September, then January is your next best option. Flight prices from Boston to Chicago during January average around $194.

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

The cheapest day to depart on your flight to Chicago is on a Friday when prices can be found for as low as $313. This is often the case because there is less demand to fly during this day of the week. When flying out on a Sunday, the most expensive travel day of the week, you can expect to see flight prices from Boston to Chicago for around $423.

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

Our most recent data shows that the best time of day to fly to Chicago is in the evening. Flights from Boston to Chicago during this time can be as low as $271. In contrast, the most expensive time of day to depart to Chicago is in the afternoon when prices are around $351.

What is the cheapest Boston Logan Intl to Chicago flight route?

Fly from Boston Logan Intl to Chicago Midway for the best Boston Logan Intl - Chicago flight prices

How far in advance should I book a flight to Chicago?

You are more likely to see cheaper flights to Chicago from Boston when booking weeks ahead of your departure date. In general, you can expect to find flights to Chicago for around $244 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Boston for as low as $210 on momondo.

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

There are 4 cabin classes available to choose from on Boston Logan Intl to Chicago 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 flight prices changed over time?

As of August 2025, prices for Boston to Chicago flights are approximately 27% cheaper when compared to flights at the same time last year.

When to book flights from Boston to Chicago

Are you open to changing your travel dates? Check out the ideal times to fly from Boston to Chicago according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Boston to Chicago (BOS to CHI) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Boston to Chicago

Best Price Found

$34

Fastest flight time

2h 30m

Direct flights

Every day

Airports in Chicago

2 airports
The best one-way flight to Chicago from Boston in the past 72 hours is $34. The best round-trip flight deal from Boston to Chicago found on momondo in the last 72 hours is $67.
The fastest flight from Boston to Chicago takes 2h 30m
Direct flights go from Boston to Chicago every day.
There are 2 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW)
Search flight deals

  • How far is Boston Logan Intl to Chicago by plane?

    A flight from Boston Logan Intl to Chicago will travel around 847.9 mi. 2h 30m is a normal flight duration for this route.

  • When did momondo last update prices for flights from Boston Logan Intl Airport to Chicago?

    Prices for flights from Boston Logan Intl Airport to Chicago refresh daily.

  • How many operators does momondo search for flights from Boston Logan Intl Airport to Chicago?

  • How old do you have to be to fly from Boston Logan Intl Airport to Chicago?

    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.

  • What documentation or ID do you need to fly to Chicago?

    The necessary travel and health documents for your Chicago trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Boston to Chicago?

  • What is the most popular airline from Boston to Chicago?

Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $35Free CancellationRating
6.3
8,054 reviews
Search Spirit Airlines flights
JetBluePriceFrom $75Free CancellationRating
7.2
2,914 reviews
Search JetBlue flights
DeltaPriceFrom $95Free CancellationRating
8.0
7,987 reviews
Search Delta flights
United AirlinesPriceFrom $97Free CancellationRating
7.4
8,915 reviews
Search United Airlines flights
FrontierPriceFrom $100Free CancellationRating
5.8
3,232 reviews
Search Frontier flights
SouthwestPriceFrom $125Free CancellationRating
8.0
4,246 reviews
Search Southwest flights
American AirlinesPriceFrom $137Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights

  • Delta Flights From Boston to Chicago

    The lowest priced Delta flight from Boston to Chicago from the last 72 hours was $95. Generally, Delta has 11 flights on this route every week with an average price of $300. Delta is rated 8.0/10 by our users.

  • Southwest Flights From Boston to Chicago

    Southwest is also a popular choice for this route. Southwest flight deals for Boston to Chicago start from as low as $125 round-trip, depending on your selected dates, with average Southwest deals seen on momondo around $233. Southwest operates 6 flights to Chicago from Boston in an average week. Users have rated it 8.0/10 across 4,246 reviews.

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?

It is quick and easy to find Boston to Chicago flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Chicago that suits you.

Can I find flights from Boston to Chicago with flexible booking policies on momondo?

momondo does allow users to show only those flights to Chicago from Boston which offer a flexible booking policy as well as other useful filters and features.

How can momondo help me find flights from Boston to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Boston. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Boston to Chicago right now. Can momondo alert me if prices change?

Price alerts on flights to Chicago from Boston are quick and easy to set up on momondo. Simply perform a search and select the price alert feature. It is as simple as that.

An easier way to manage your Chicago trip

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Find better results for your trip to the United States

Fly into one of these airports located in Chicago

Airports listed have a maximum distance of 78.5 mi from Chicago
Chicago Midway Airport
Chicago O'Hare Intl Airport
Chicago Greater Rockford Airport