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Cheap flights from Boston to Chicago from £75

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 16/8. 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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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
3 Jun
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
5 Jun
ORD19:15Chicago O'Hare Intl
2h 26m
BOS22:41Boston Logan Intl
Delta
18 Jun
BOS15:55Boston Logan Intl
2h 51m
ORD17:46Chicago O'Hare Intl
25 Jun
ORD06:30Chicago O'Hare Intl
2h 28m
BOS09:58Boston Logan Intl
United Airlines
15 Jun
BOS06:00Boston Logan Intl
2h 50m
ORD07:50Chicago O'Hare Intl
6 Jul
ORD06:00Chicago O'Hare Intl
2h 22m
BOS09:22Boston Logan Intl
American Airlines
26 Jul
BOS19:30Boston Logan Intl
2h 55m
ORD21:25Chicago O'Hare Intl
28 Jul
ORD09:55Chicago O'Hare Intl
2h 32m
BOS13:27Boston Logan Intl
Southwest
18 Jun
BOS14:30Boston Logan Intl
8h 00m
1 stop
ORD21:30Chicago O'Hare Intl
25 Jun
ORD18:00Chicago O'Hare Intl
4h 45m
1 stop
BOS23:45Boston Logan Intl
JetBlue
5 Jun
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
12 Jun
ORD09:00Chicago O'Hare Intl
2h 33m
BOS12:33Boston 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 JetBlue, Spirit Airlines and United Airlines
JetBlue
16 Aug
BOS06:00Boston Logan Intl
2h 54m
ORD07:54Chicago O'Hare Intl
Spirit Airlines
6 Jun
BOS12:07Boston Logan Intl
23h 07m
2 stops
ORD10:14Chicago O'Hare Intl
United Airlines
23 Jun
BOS06:00Boston Logan Intl
2h 47m
ORD07:47Chicago 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
JetBlue
29 May
BOS16:25Boston Logan Intl
2h 55m
ORD18:20Chicago O'Hare Intl
1 Jun
ORD17:35Chicago O'Hare Intl
5h 46m
1 stop
BOS00:21Boston Logan Intl
Delta
27 May
BOS10:15Boston Logan Intl
2h 46m
ORD12:01Chicago O'Hare Intl
1 Jun
ORD17:15Chicago O'Hare Intl
2h 29m
BOS20:44Boston Logan Intl
United Airlines
27 May
BOS08:00Boston Logan Intl
2h 50m
ORD09:50Chicago O'Hare Intl
2 Jun
ORD06:04Chicago O'Hare Intl
2h 20m
BOS09:24Boston Logan Intl
American Airlines
24 May
BOS14:07Boston Logan Intl
2h 59m
ORD16:06Chicago O'Hare Intl
26 May
ORD20:29Chicago O'Hare Intl
2h 26m
BOS23:55Boston Logan Intl
JetBlue
29 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
28 May
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
29 May
ORD17:32Chicago O'Hare Intl
4h 37m
1 stop
BOS23:09Boston Logan Intl

JetBlue flights from Boston to Chicago

Our best JetBlue deals on Boston to Chicago flight tickets
JetBlue
3 Jun
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
5 Jun
ORD19:15Chicago O'Hare Intl
2h 26m
BOS22:41Boston Logan Intl
JetBlue
5 Jun
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
12 Jun
ORD09:00Chicago O'Hare Intl
2h 33m
BOS12:33Boston Logan Intl
JetBlue
15 Jul
BOS06:00Boston Logan Intl
2h 54m
ORD07:54Chicago O'Hare Intl
30 Jul
ORD17:15Chicago O'Hare Intl
6h 02m
1 stop
BOS00:17Boston Logan Intl

Delta flights from Boston to Chicago

Our best Delta deals on Boston to Chicago flight tickets
Delta
18 Jun
BOS15:55Boston Logan Intl
2h 51m
ORD17:46Chicago O'Hare Intl
25 Jun
ORD06:30Chicago O'Hare Intl
2h 28m
BOS09:58Boston Logan Intl
Delta
31 Oct
BOS17:40Boston Logan Intl
2h 49m
ORD19:29Chicago O'Hare Intl
6 Nov
ORD17:27Chicago O'Hare Intl
2h 24m
BOS20:51Boston Logan Intl
Delta
2 Aug
BOS19:40Boston Logan Intl
2h 59m
ORD21:39Chicago O'Hare Intl
5 Aug
ORD06:30Chicago O'Hare Intl
2h 12m
BOS09:42Boston 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 Thursday.

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

In the afternoon. Boston to Chicago flights are approximately 28% 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?

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

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

£75

Fastest flight time

2h 45m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Boston in the past 72 hours is £75. The best return flight deal from Boston to Chicago found on momondo in the last 72 hours is £139.
The fastest flight from Boston to Chicago takes 2h 45m
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 10m 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 train to be one of the cheapest options available to you for travel. Currently, a train has deals available from £118. While they may not be the most cost-effective options currently available a flight 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 45m 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.


Choose the best way to get from Boston to Chicago

Buses

27h 35m
£87 one-way£140 return
Direct · from £140

Distance to city centre

ZUN0.7 mi

Find Buses

Boston to Chicago Buses

Trains

22h 15m
£77 one-way£154 return
Direct · from £154

Distance to city centre

ZUN0.7 mi

Find Trains

Boston to Chicago Trains

Flights

2h 47m
£75 one-way£139 return
Direct · from £1391 stop · from £83

Distance to city centre

ORD15.9 mi

An easier way to manage your Chicago trip

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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