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Cheap flights from Boston to Chicago from £54

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 30/5. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags
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Wed 22/5
Wed 29/5
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Easily compare return flights from Boston to Chicago

Below you can see the best fares for your return flight route over the next six months. All fares were found on momondo this week. Browse the quickest and cheapest flights from Boston to Chicago by changing tabs
JetBlue
1 Jul
BOS06:00Boston Logan Intl
2h 54m
ORD07:54Chicago O'Hare Intl
4 Jul
ORD10:35Chicago O'Hare Intl
8h 32m
1 stop
BOS20:07Boston Logan Intl
Delta
4 Jun
BOS06:25Boston Logan Intl
2h 55m
ORD08:20Chicago O'Hare Intl
8 Jun
ORD17:52Chicago O'Hare Intl
2h 40m
BOS21:32Boston Logan Intl
Spirit Airlines
22 Jul
BOS06:35Boston Logan Intl
2h 54m
ORD08:29Chicago O'Hare Intl
24 Jul
ORD21:30Chicago O'Hare Intl
2h 28m
BOS00:58Boston Logan Intl
United Airlines
30 May
BOS08:00Boston Logan Intl
2h 50m
ORD09:50Chicago O'Hare Intl
31 May
ORD21:45Chicago O'Hare Intl
2h 35m
BOS01:20Boston Logan Intl
American Airlines
22 Jul
BOS05:15Boston Logan Intl
2h 56m
ORD07:11Chicago O'Hare Intl
24 Jul
ORD20:28Chicago O'Hare Intl
2h 20m
BOS23:48Boston Logan Intl
Southwest
24 Jun
BOS05:55Boston Logan Intl
4h 30m
1 stop
ORD09:25Chicago O'Hare Intl
26 Jun
ORD18:00Chicago O'Hare Intl
4h 45m
1 stop
BOS23:45Boston 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
30 May
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
Delta
19 Jul
BOS19:40Boston Logan Intl
2h 59m
ORD21:39Chicago O'Hare Intl
United Airlines
27 Jun
BOS06:00Boston Logan Intl
2h 50m
ORD07:50Chicago O'Hare Intl

Search last-minute flights to Chicago from Boston

Find and compare return flight prices for your last-minute flight from Boston to Chicago
Delta
26 May
BOS12:50Boston Logan Intl
2h 59m
ORD14:49Chicago O'Hare Intl
11 Jun
ORD06:30Chicago O'Hare Intl
2h 28m
BOS09:58Boston Logan Intl
JetBlue
26 May
BOS16:25Boston Logan Intl
2h 55m
ORD18:20Chicago O'Hare Intl
31 May
ORD19:15Chicago O'Hare Intl
2h 26m
BOS22:41Boston Logan Intl
American Airlines
24 May
BOS07:20Boston Logan Intl
4h 51m
1 stop
ORD11:11Chicago O'Hare Intl
26 May
ORD08:10Chicago O'Hare Intl
2h 22m
BOS11:32Boston Logan Intl
United Airlines
25 May
BOS18:01Boston Logan Intl
5h 59m
1 stop
ORD23:00Chicago O'Hare Intl
2 Jun
ORD06:04Chicago O'Hare Intl
2h 20m
BOS09:24Boston Logan Intl
Southwest
21 May
BOS06:05Boston Logan Intl
9h 10m
1 stop
ORD14:15Chicago O'Hare Intl
23 May
ORD06:15Chicago O'Hare Intl
6h 40m
1 stop
BOS13:55Boston Logan Intl
JetBlue
26 May
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
31 May
ORD19:15Chicago O'Hare Intl
2h 26m
BOS22:41Boston Logan Intl

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets
JetBlue
1 Jul
BOS06:00Boston Logan Intl
2h 54m
ORD07:54Chicago O'Hare Intl
4 Jul
ORD10:35Chicago O'Hare Intl
8h 32m
1 stop
BOS20:07Boston Logan Intl
JetBlue
9 Jul
BOS05:15Boston Logan Intl
5h 36m
1 stop
ORD09:51Chicago O'Hare Intl
16 Jul
ORD10:37Chicago O'Hare Intl
8h 25m
1 stop
BOS20:02Boston Logan Intl
JetBlue
29 May
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
30 May
ORD08:40Chicago O'Hare Intl
2h 29m
BOS12:09Boston Logan Intl

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets
Delta
4 Jun
BOS06:25Boston Logan Intl
2h 55m
ORD08:20Chicago O'Hare Intl
8 Jun
ORD17:52Chicago O'Hare Intl
2h 40m
BOS21:32Boston Logan Intl
Delta
26 May
BOS12:50Boston Logan Intl
2h 59m
ORD14:49Chicago O'Hare Intl
11 Jun
ORD06:30Chicago O'Hare Intl
2h 28m
BOS09:58Boston Logan Intl
Delta
3 Jun
BOS06:25Boston Logan Intl
2h 55m
ORD08:20Chicago O'Hare Intl
8 Jun
ORD17:52Chicago O'Hare Intl
2h 40m
BOS21:32Boston Logan Intl

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?

January. The cheapest time of year to fly to Chicago from Boston is January. The most expensive is June.

What is the cheapest day to depart Boston for Chicago?

Wednesday. The cheapest day of the week is usually Wednesday. The most expensive is usually Tuesday.

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

In the afternoon. Boston to Chicago flights are approximately 25% more expensive in the morning than in the afternoon

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?

51 days before. The cheapest time to buy a flight from Boston to Chicago is approximately 51 days to departure

How many flights depart from Boston to Chicago on average per day?

51 flights are operational weekly from Boston to Chicago as of May 2024. The most popular departure time for this route is 07:00, with 42% of flights per day taking off in the afternoon.

How many flights depart from Boston to Chicago on average per week?

The number of flights available between Boston and Chicago is 363 per week as of May 2024. The most frequent departure day is Monday, with 18% of weekly flights leaving on this day.

Can stopping save me money on Boston to Chicago flights?

You could potentially save up to 13% on your flight if you consider stops on a Boston to Chicago flight.

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

£54

Fastest flight time

2h 46m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Boston in the past 72 hours is £54. The best return flight deal from Boston to Chicago found on momondo in the last 72 hours is £115.
The fastest flight from Boston to Chicago takes 2h 46m
Direct flights go from Boston to Chicago every day.
There is 1 airport near Chicago: Chicago O'Hare Intl (ORD)

  • 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 25h 09m 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 £115. 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. 2h 46m 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 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.


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.


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Find better results for your stay in the United States

Fly into one of these airports located in Chicago
Airports listed have a maximum distance of 78.5 mi from Chicago