Cheap flights from Boston to Chicago from $57

Round-trip
1 adult
Economy
From?
To?
Mon 5/30
Mon 6/6

Deals available from 900+ travel sites.

Flight information for Boston to Chicago
(BOS to CHI)

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

Best Price Found

$57

Fastest flight time

2h 40m

Direct flights

Mon, Tue, Thu, Fri, Sat and Sun

Airports in Chicago

3 airports
The best one-way flight to Chicago from Boston in the past 72 hours is $57. The best round-trip flight deal from Boston to Chicago found on momondo in the last 72 hours is $128.
The fastest flight from Boston to Chicago takes 2h 40m
Direct flights go from Boston to Chicago on Monday, Tuesday, Thursday, Friday, Saturday and Sunday. Airlines offering direct flights are: Southwest and American Airlines.
There are 3 airports near Chicago: Chicago O'Hare Intl (ORD), Chicago Midway (MDW), Chicago Greater Rockford (RFD)

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 from Boston to Chicago?

August

The cheapest time of year to fly to Chicago from Boston is August. Most expensive is December

What is the cheapest day to depart Boston for Chicago?

Tuesday

The cheapest day of the week is typically Tuesday. The most expensive is typically Friday

When is the cheapest time to fly from Boston to Chicago?

in the evening

Boston to Chicago flights are approximately 20% more expensive in the afternoon than in the evening

What is the cheapest airline that flies to Chicago from Boston?

Juneyao Airlines

American Airlines, Delta, and JetBlue are the most popular carriers operating from Boston to Chicago

What is the cheapest Boston to Chicago flight route?

Boston Logan Intl - Chicago O'Hare Intl

Fly from Boston Logan Intl to Chicago O'Hare Intl for the best Boston - Chicago flight prices

How far in advance should you book Boston to Chicago flights?

0 days before

The cheapest time to buy a flight from Boston to Chicago is approximately 0 days to departure

Boston Logan Intl Airport (BOS) to Chicago O'Hare Intl Airport (ORD)$128
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Boston Logan Intl Airport (BOS) to Chicago Midway Airport (MDW)$146
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Providence-TFGreen Airport (PVD) to Chicago O'Hare Intl Airport (ORD)$225
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Providence-TFGreen Airport (PVD) to Chicago Midway Airport (MDW)$355
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Boston Logan Intl Airport (BOS) to Chicago Greater Rockford Airport (RFD)$468
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When you’re planning your trip from Boston to Chicago, the most popular airport-to-airport route is Boston Logan Intl Airport to Chicago O'Hare Intl Airport. If you are looking for alternate airports to fly out of when traveling to Chicago, you can try Boston Logan Intl Airport or Providence-TFGreen Airport which are located in Boston and Providence respectively. When traveling from Boston, it is helpful to have an alternative airport to fly into when you land in Chicago. Good options for arrival airports in Chicago, you can try Chicago Midway Airport (in Chicago), Chicago O'Hare Intl Airport (in Chicago), or Chicago Greater Rockford Airport (in Chicago). The cheapest route from Boston to Chicago is BOS — ORD with an average price of $128 RT during the month of May.


Easily compare round-trip flights from Boston to Chicago

Below you can see the best fares for your round-trip flight route over the next three months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Boston to Chicago by changing tabs
JetBlue
Sep 24
BOS2:20 amBoston Logan Intl
2h 54m
ORD5:14 amChicago O'Hare Intl
Oct 1
ORD3:45 pmChicago O'Hare Intl
2h 24m
BOS6:09 pmBoston Logan Intl
Delta
Sep 24
BOS2:45 amBoston Logan Intl
3h 09m
ORD5:54 amChicago O'Hare Intl
Sep 24
ORD1:55 pmChicago O'Hare Intl
6h 06m
1 stop
BOS8:01 pmBoston Logan Intl
Multiple Airlines
Oct 5
BOS1:40 amBoston Logan Intl
4h 39m
1 stop
ORD6:19 amChicago O'Hare Intl
Oct 15
ORD3:45 pmChicago O'Hare Intl
2h 24m
BOS6:09 pmBoston Logan Intl
American Airlines
Aug 23
BOS4:00 amBoston Logan Intl
3h 01m
ORD7:01 amChicago O'Hare Intl
Aug 30
ORD4:50 amChicago O'Hare Intl
5h 49m
1 stop
BOS10:39 amBoston Logan Intl
United Airlines
Aug 23
BOS3:31 amBoston Logan Intl
2h 50m
ORD6:21 amChicago O'Hare Intl
Aug 30
ORD2:00 amChicago O'Hare Intl
2h 21m
BOS4:21 amBoston Logan Intl
Southwest
Aug 26
BOS6:40 pmBoston Logan Intl
2h 50m
MDW9:30 pmChicago Midway
Sep 10
MDW2:55 pmChicago Midway
2h 10m
BOS5:05 pmBoston Logan Intl

Find the cheapest one-way flights from Boston to Chicago

If you're looking for one-way flights from Boston to Chicago, view some of our deals below provided by Delta, JetBlue and United Airlines
JetBlue
Jun 7
BOS10:01 amBoston Logan Intl
2h 58m
ORD12:59 pmChicago O'Hare Intl
Delta
Oct 4
BOS1:05 pmBoston Logan Intl
3h 12m
ORD4:17 pmChicago O'Hare Intl
United Airlines
Jun 1
BOS2:22 pmBoston Logan Intl
2h 59m
ORD5:21 pmChicago O'Hare Intl

Search last-minute flights to Chicago from Boston

Find and compare round-trip flight prices for your last-minute flight from Boston to Chicago
Spirit Airlines
Jun 1
BOS5:53 amBoston Logan Intl
10h 05m
1 stop
ORD3:58 pmChicago O'Hare Intl
Jun 8
ORD7:05 amChicago O'Hare Intl
7h 41m
1 stop
BOS2:46 pmBoston Logan Intl
Multiple Airlines
Jun 1
BOS1:30 amBoston Logan Intl
2h 54m
ORD4:24 amChicago O'Hare Intl
Jun 8
ORD7:05 amChicago O'Hare Intl
7h 41m
1 stop
BOS2:46 pmBoston Logan Intl
American Airlines
May 30
BOS1:30 amBoston Logan Intl
2h 54m
ORD4:24 amChicago O'Hare Intl
May 31
ORD1:10 pmChicago O'Hare Intl
2h 18m
BOS3:28 pmBoston Logan Intl
JetBlue
Jun 1
BOS10:01 amBoston Logan Intl
2h 55m
ORD12:56 pmChicago O'Hare Intl
Jun 4
ORD9:14 amChicago O'Hare Intl
7h 42m
1 stop
BOS4:56 pmBoston Logan Intl
Delta
Jun 1
BOS2:30 amBoston Logan Intl
2h 59m
ORD5:29 amChicago O'Hare Intl
Jun 2
ORD2:00 amChicago O'Hare Intl
6h 30m
1 stop
BOS8:30 amBoston Logan Intl
Frontier
Jun 4
BOS8:23 amBoston Logan Intl
21h 11m
1 stop
MDW5:34 amChicago Midway
Jun 7
MDW5:39 amChicago Midway
24h 11m
1 stop
BOS5:50 amBoston Logan Intl

Best airlines flying from Boston to Chicago

Compare and see reviews for airlines that fly from Boston to Chicago with momondo
AirlineRatingFree CancellationPrice
Juneyao AirlinesPriceFrom $14Free CancellationRating
0.0
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Spirit AirlinesPriceFrom $52Free CancellationRating
6.2
6.4

Boarding

5.8

Comfort

6.9

Crew

4.8

Entertainment

5.1

Food

Reviews

Easy-going and relaxing crew. Seats were not super comfortable. But adequate.

1 / 10
Search Spirit Airlines flights
JetBluePriceFrom $58Free CancellationRating
6.9
7.1

Boarding

7.4

Comfort

7.8

Crew

7.1

Entertainment

6.6

Food

Reviews

I did not like anything. You can not cancel the flight 6hrs after delaying the flight. You can provide hotel rooms and shuttle services if you decide to cancel for no apparent reason in the middle of the night. The WORSE experience ever. No body wants jet blue bank "money" give me real money to pay for the extra expenses cause by YOU!!!! Jet Blue is now a no on my list. Will never be my choice to flight.

1 / 10
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DeltaPriceFrom $74Free CancellationRating
7.9
7.9

Boarding

8.0

Comfort

8.3

Crew

7.7

Entertainment

7.3

Food

Reviews

This is another disease as if you have the Internet, you are ordinary deceivers!

1 / 10
Search Delta flights
United AirlinesPriceFrom $83Free CancellationRating
7.4
7.6

Boarding

7.2

Comfort

8.0

Crew

6.9

Entertainment

6.7

Food

Reviews

Boarding process was confusing. No signage or any announcement of where the groups should be lined up. Flight crew was excellent. Very attentive. Service was excellent.

1 / 10
Search United Airlines flights
American AirlinesPriceFrom $97Free CancellationRating
7.3
7.7

Boarding

7.2

Comfort

8.1

Crew

7.0

Entertainment

6.5

Food

Reviews

Great flight...early arrival. Need more food options

1 / 10
Search American Airlines flights
Alaska AirlinesPriceFrom $249Free CancellationRating
8.0
8.3

Boarding

8.0

Comfort

8.5

Crew

7.4

Entertainment

7.2

Food

Reviews

Kayak reservation did not have a filed for add known traveler number. Hence, TSA pre-check did not work and resulted in 25+ minutes wait for TSA.

1 / 10
Search Alaska Airlines flights
  • Alaska Airlines Flights From Boston to Chicago

    The lowest priced Alaska Airlines flight from Boston to Chicago from the last 72 hours was $249. Generally, Alaska Airlines has 28 flights on this route every week with an average price of $366. Alaska Airlines is rated 8.0/10 by our users.

  • Delta Flights From Boston to Chicago

    Delta is also a popular choice for this route. Delta flight deals for Boston to Chicago start from as low as $74 round-trip, depending on your selected dates, with average Delta deals seen on momondo around $259. Delta operates 22 flights to Chicago from Boston in an average week. Users have rated it 7.9/10 across 385 reviews.


Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets
Delta
Sep 24
BOS2:45 amBoston Logan Intl
3h 09m
ORD5:54 amChicago O'Hare Intl
Sep 24
ORD1:55 pmChicago O'Hare Intl
6h 06m
1 stop
BOS8:01 pmBoston Logan Intl
Delta
Sep 24
BOS1:40 amBoston Logan Intl
4h 39m
1 stop
ORD6:19 amChicago O'Hare Intl
Sep 24
ORD1:55 pmChicago O'Hare Intl
6h 06m
1 stop
BOS8:01 pmBoston Logan Intl
Delta
Oct 1
BOS2:45 amBoston Logan Intl
3h 09m
ORD5:54 amChicago O'Hare Intl
Oct 5
ORD3:05 amChicago O'Hare Intl
6h 21m
1 stop
BOS9:26 amBoston Logan Intl

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets
JetBlue
Sep 24
BOS2:20 amBoston Logan Intl
2h 54m
ORD5:14 amChicago O'Hare Intl
Oct 1
ORD3:45 pmChicago O'Hare Intl
2h 24m
BOS6:09 pmBoston Logan Intl
JetBlue
Oct 1
BOS12:55 pmBoston Logan Intl
3h 00m
ORD3:55 pmChicago O'Hare Intl
Oct 5
ORD3:45 pmChicago O'Hare Intl
2h 24m
BOS6:09 pmBoston Logan Intl
JetBlue
Sep 22
BOS2:20 amBoston Logan Intl
2h 54m
ORD5:14 amChicago O'Hare Intl
Sep 26
ORD4:59 amChicago O'Hare Intl
2h 21m
BOS7:20 amBoston Logan Intl

  • Are airlines flying from Boston Logan Intl to Chicago offering flexible cancellation due to COVID-19?

    Due to the global impact of COVID-19, some of our airline partners operating flights from Boston Logan Intl to Chicago, such as United Airlines, JetBlue, and American Airlines may have put in place flexible cancellation policies. Use our site to search for all of the airlines offering this flexibility to you.

  • 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 35m is a normal flight duration for this route.



Alternative routes for Boston to Chicago

Compare alternative flights to and from nearby airports and cities to discover the best prices and most convenient flight times
Boston to St. Louis Flights
Fastest flight time3h 01m
Cheapest price$275

Similar Boston to Chicago flights

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Why use momondo?

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.

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.

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.

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