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Cheap flights from Boston to Chicago from £51

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 6/2. 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 return flights

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Delta Logo
11:30 - 13:39
BOS
-
ORD
3h 09mdirect
Delta Logo
14:25 - 17:54
ORD
-
BOS
2h 29mdirect
£92Delta
Thu, 5 Feb - Mon, 9 Feb
Delta Logo
07:30 - 09:41
BOS
-
ORD
3h 11mdirect
Delta Logo
14:00 - 17:29
ORD
-
BOS
2h 29mdirect
£93Delta
Sun, 25 Jan - Sat, 31 Jan
Delta Logo
12:55 - 16:57
BOS
-
ORD
5h 02m1 stop
Delta Logo
07:10 - 13:22
ORD
-
BOS
5h 12m1 stop
£94Delta
Wed, 4 Feb - Thu, 5 Feb
JetBlue Logo
15:35 - 17:43
BOS
-
ORD
3h 08mdirect
JetBlue Logo
07:40 - 11:05
ORD
-
BOS
2h 25mdirect
£95JetBlue
Sat, 17 Jan - Tue, 20 Jan
Delta Logo
12:00 - 18:28
BOS
-
ORD
7h 28m1 stop
Delta Logo
10:35 - 15:53
ORD
-
BOS
4h 18m1 stop
£95Delta
Thu, 5 Feb - Mon, 9 Feb
Delta Logo
18:35 - 23:56
BOS
-
ORD
6h 21m1 stop
Delta Logo
07:05 - 10:40
ORD
-
BOS
2h 35mdirect
£97Delta
Thu, 29 Jan - Mon, 2 Feb
JetBlue Logo
15:20 - 17:24
BOS
-
ORD
3h 04mdirect
JetBlue Logo
10:00 - 13:27
ORD
-
BOS
2h 27mdirect
£98JetBlue
Mon, 23 Mar - Wed, 1 Apr
JetBlue Logo
15:35 - 17:43
BOS
-
ORD
3h 08mdirect
JetBlue Logo
07:45 - 11:10
ORD
-
BOS
2h 25mdirect
£98JetBlue
Tue, 20 Jan - Sun, 25 Jan
JetBlue Logo
14:50 - 16:55
BOS
-
ORD
3h 05mdirect
JetBlue Logo
10:00 - 13:20
ORD
-
BOS
2h 20mdirect
£99JetBlue
Wed, 11 Feb - Fri, 13 Feb
Delta Logo
12:00 - 16:30
BOS
-
ORD
5h 30m1 stop
Delta Logo
10:40 - 14:13
ORD
-
BOS
2h 33mdirect
£100Delta
Thu, 5 Feb - Mon, 9 Feb

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets
JetBlue
17 Jan
BOS15:35Boston Logan Intl
3h 08m
ORD17:43Chicago O'Hare Intl
20 Jan
ORD07:40Chicago O'Hare Intl
2h 25m
BOS11:05Boston Logan Intl
£95
Find similar
JetBlue
20 Jan
BOS15:35Boston Logan Intl
3h 08m
ORD17:43Chicago O'Hare Intl
25 Jan
ORD07:45Chicago O'Hare Intl
2h 25m
BOS11:10Boston Logan Intl
£98
Find similar
JetBlue
11 Feb
BOS14:50Boston Logan Intl
3h 05m
ORD16:55Chicago O'Hare Intl
13 Feb
ORD10:00Chicago O'Hare Intl
2h 20m
BOS13:20Boston Logan Intl
£99
Find similar

Southwest flights from Boston to Chicago

Our best Southwest deals on Boston to Chicago flight tickets
Southwest
24 Jan
BOS05:10Boston Logan Intl
8h 05m
1 stop
ORD12:15Chicago O'Hare Intl
24 Jan
ORD13:45Chicago O'Hare Intl
5h 45m
1 stop
BOS20:30Boston Logan Intl
£104
Find similar
Southwest
10 Jan
BOS05:10Boston Logan Intl
8h 05m
1 stop
ORD12:15Chicago O'Hare Intl
12 Jan
ORD13:45Chicago O'Hare Intl
7h 00m
1 stop
BOS21:45Boston Logan Intl
£135
Find similar

momondo Fare Finder

 
Customise 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 279,928 searches. Data last updated 7 January 2026.
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 - ORD

BOSORD

Boston Logan Intl

Thu 5/2

11:30-13:39

Nonstop3h 09m

Chicago O'Hare Intl

Mon 9/2

14:25-17:54

Nonstop2h 29m

£92

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 25/1

07:30-09:41

Nonstop3h 11m

Chicago O'Hare Intl

Sat 31/1

14:00-17:29

Nonstop2h 29m

£93

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 4/2

12:55-16:57

1 stop5h 02m

Chicago O'Hare Intl

Thu 5/2

07:10-13:22

1 stop5h 12m

£94

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 17/1

15:35-17:43

Nonstop3h 08m

Chicago O'Hare Intl

Tue 20/1

07:40-11:05

Nonstop2h 25m

£95

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/2

12:00-18:28

1 stop7h 28m

Chicago O'Hare Intl

Mon 9/2

10:35-15:53

1 stop4h 18m

£95

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 29/1

18:35-23:56

1 stop6h 21m

Chicago O'Hare Intl

Mon 2/2

07:05-10:40

Nonstop2h 35m

£97

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 23/3

15:20-17:24

Nonstop3h 04m

Chicago O'Hare Intl

Wed 1/4

10:00-13:27

Nonstop2h 27m

£98

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 20/1

15:35-17:43

Nonstop3h 08m

Chicago O'Hare Intl

Sun 25/1

07:45-11:10

Nonstop2h 25m

£98

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 11/2

14:50-16:55

Nonstop3h 05m

Chicago O'Hare Intl

Fri 13/2

10:00-13:20

Nonstop2h 20m

£99

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 5/2

12:00-16:30

1 stop5h 30m

Chicago O'Hare Intl

Mon 9/2

10:40-14:13

Nonstop2h 33m

£100

Flights are sorted by cheapest return flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
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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 typical price of a round-trip flight between Boston and Chicago?

What is the cheapest month to fly to Chicago?

The cheapest month to fly to Chicago from Boston is in September. Flight prices, which tend to average around £138, are often lower during this time because this is during the off-season. If you aren’t able to travel during the month of September, then book flights to Chicago from Boston during January instead. Flights to Chicago in January, while not as cheap as those in September, still average around £149.

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 Thursday when prices can be found for as low as £152. This is often the case because there is less demand to fly during this day of the week. The most expensive day to fly to Chicago is Tuesday, with ticket prices averaging around £629.

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

Flying to Chicago from Boston in the evening is the least expensive time of day to depart. momondo users have found prices as low as £127 when looking at flights departing in the evening. Flights in the afternoon are often more expensive, with an average ticket price of £375.

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

Fly from Boston Logan Intl to Chicago O'Hare Intl 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 £184 when searching weeks before you fly. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Chicago from Boston for as low as £164 on momondo.

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

There are 3 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.

Can stopping save me money on Boston to Chicago flights?

No. A direct flight is the cheapest option for a flight between Boston to Chicago.

How have Boston to Chicago flight prices changed over time?

As of January 2026, prices for Boston to Chicago flights are approximately 7% more expensive 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 return 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

£121

Fastest flight time

3h 03m

Direct flights

Every day

Airports in Chicago

3 airports
The best one-way flight to Chicago from Boston in the past 72 hours is £121. The best return flight deal from Boston to Chicago found on momondo in the last 72 hours is £111.
The fastest flight from Boston to Chicago takes 3h 03m
Direct flights go from Boston to Chicago every day.
There are 3 airports in Chicago. From Boston there are direct flights to Chicago O'Hare Intl (ORD).
Search flight deals

  • Is flying the fastest way to get from Boston to Chicago?

    The quickest way to travel this route is to take a flight from Boston to Chicago, doing so can potentially save up to 24h 41m of travel time. While these options may take longer, booking a train from Boston to Chicago or a bus from Boston to Chicago may suit your needs if travel time is less of a factor in your decision making.

  • Is flying the cheapest way to get from Boston to Chicago?

    Expect a flight to be one of the cheapest options available to you for travel. Currently, a flight has deals available from £92. While they may not be the most cost-effective options currently available a train from Boston to Chicago or a bus from Boston to Chicago can also be options worth looking into if other factors outside of cost are a higher priority.

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

    Chicago is 847.9 mi away from Boston Logan Intl. 3h 03m 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 were last updated today.

  • 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?

    Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify 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 travel and health documents you'll need for your trip to Chicago 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. 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?

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
American AirlinesPriceFrom £73Free CancellationRating
7.2
11,088 reviews
Search American Airlines flights

  • American Airlines Flights From Boston to Chicago

    American Airlines operates around 21 flights from Boston to Chicago every week. The average price of these flights found in the last 72 hours has been £114, but momondo users have found American Airlines deals from Boston to Chicago from as low as £73 round-trip. American Airlines has been scored 7.2/10 in 11,088 reviews.

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?

Flights from Boston to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

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

momondo helps you find the best flight between Boston and Chicago by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

If you are simply researching potential flights to Chicago, momondo offers a useful price alert feature which will track prices for flights to Chicago from Boston and alert you when they change.

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