Insights
Latest deals
FAQs

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 29/5. 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
From?
To?
Thu 2/5
Thu 9/5
'This year, momondo is the #1 place for airfares on the internet.'
Voted winner of Europe's Best Travel App 2023
Save money when you book flights with momondo
Big names, great deals
Big names, great deals
Search 100s of travel sites to compare prices.
Filter for what you want
Filter for what you want
Free Wi-Fi? Stopover? Instantly customise your results.
Trusted and free
Trusted and free
We’re completely free to use - no hidden charges or fees.
Price Alerts
Price Alerts
Not ready to book? Create a price alert to track prices.

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
Spirit Airlines
12 Jun
BOS06:30Boston Logan Intl
2h 54m
ORD08:24Chicago O'Hare Intl
22 Jun
ORD20:39Chicago O'Hare Intl
2h 29m
BOS00:08Boston Logan Intl
JetBlue
29 May
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
29 May
ORD19:15Chicago O'Hare Intl
2h 26m
BOS22:41Boston Logan Intl
United Airlines
22 May
BOS08:00Boston Logan Intl
2h 52m
ORD09:52Chicago O'Hare Intl
29 May
ORD21:45Chicago O'Hare Intl
2h 35m
BOS01:20Boston Logan Intl
Delta
28 May
BOS06:25Boston Logan Intl
2h 55m
ORD08:20Chicago O'Hare Intl
29 May
ORD06:27Chicago O'Hare Intl
2h 27m
BOS09:54Boston Logan Intl
Southwest
28 May
BOS18:00Boston Logan Intl
5h 20m
1 stop
ORD22:20Chicago O'Hare Intl
29 May
ORD10:30Chicago O'Hare Intl
11h 40m
1 stop
BOS23:10Boston Logan Intl
American Airlines
9 May
BOS07:10Boston Logan Intl
3h 04m
ORD09:14Chicago O'Hare Intl
13 May
ORD20:29Chicago O'Hare Intl
2h 26m
BOS23:55Boston 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 Spirit Airlines
JetBlue
29 May
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
Delta
28 May
BOS14:10Boston Logan Intl
2h 54m
ORD16:04Chicago O'Hare Intl
Spirit Airlines
4 Oct
BOS07:00Boston Logan Intl
2h 33m
ORD08:33Chicago 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
11 May
BOS16:35Boston Logan Intl
2h 55m
ORD18:30Chicago O'Hare Intl
14 May
ORD08:40Chicago O'Hare Intl
2h 29m
BOS12:09Boston Logan Intl
American Airlines
4 May
BOS17:30Boston Logan Intl
2h 56m
ORD19:26Chicago O'Hare Intl
11 May
ORD20:39Chicago O'Hare Intl
2h 26m
BOS00:05Boston Logan Intl
Delta
11 May
BOS16:25Boston Logan Intl
2h 52m
ORD18:17Chicago O'Hare Intl
28 May
ORD17:15Chicago O'Hare Intl
2h 29m
BOS20:44Boston Logan Intl
United Airlines
4 May
BOS10:07Boston Logan Intl
5h 38m
1 stop
ORD14:45Chicago O'Hare Intl
11 May
ORD07:00Chicago O'Hare Intl
6h 40m
1 stop
BOS14:40Boston Logan Intl
JetBlue
8 May
BOS06:10Boston Logan Intl
2h 54m
ORD08:04Chicago O'Hare Intl
11 May
ORD08:40Chicago O'Hare Intl
2h 29m
BOS12:09Boston Logan Intl
Southwest
1 May
BOS06:30Boston Logan Intl
12h 25m
1 stop
ORD17:55Chicago O'Hare Intl
2 May
ORD07:15Chicago O'Hare Intl
9h 55m
1 stop
BOS18:10Boston Logan Intl

Spirit Airlines flights from Boston to Chicago

Our best Spirit Airlines deals on Boston to Chicago flight tickets
Spirit Airlines
12 Jun
BOS06:30Boston Logan Intl
2h 54m
ORD08:24Chicago O'Hare Intl
22 Jun
ORD20:39Chicago O'Hare Intl
2h 29m
BOS00:08Boston Logan Intl
Spirit Airlines
12 Jun
BOS06:10Boston Logan Intl
12h 30m
1 stop
ORD17:40Chicago O'Hare Intl
22 Jun
ORD20:39Chicago O'Hare Intl
2h 29m
BOS00:08Boston Logan Intl
Spirit Airlines
12 Jun
BOS05:45Boston Logan Intl
17h 07m
2 stops
ORD21:52Chicago O'Hare Intl
22 Jun
ORD20:39Chicago O'Hare Intl
2h 29m
BOS00:08Boston Logan Intl

United Airlines flights from Boston to Chicago

Our best United Airlines deals on Boston to Chicago flight tickets
United Airlines
22 May
BOS08:00Boston Logan Intl
2h 52m
ORD09:52Chicago O'Hare Intl
29 May
ORD21:45Chicago O'Hare Intl
2h 35m
BOS01:20Boston Logan Intl
United Airlines
22 May
BOS08:00Boston Logan Intl
2h 52m
ORD09:52Chicago O'Hare Intl
29 May
ORD06:00Chicago O'Hare Intl
6h 15m
1 stop
BOS13:15Boston Logan Intl
United Airlines
22 May
BOS05:45Boston Logan Intl
4h 54m
1 stop
ORD09:39Chicago O'Hare Intl
29 May
ORD06:00Chicago O'Hare Intl
6h 15m
1 stop
BOS13:15Boston 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 evening. Boston to Chicago flights are approximately 57% more expensive in the morning than in the evening

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?

54 days before. The cheapest time to buy a flight from Boston to Chicago is approximately 54 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 April 2024. The most popular departure time for this route is 07:00, with 55% 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 April 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 14% 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

£51

Fastest flight time

2h 33m

Direct flights

Every day

Airports in Chicago

1 airport
The best one-way flight to Chicago from Boston in the past 72 hours is £51. The best return flight deal from Boston to Chicago found on momondo in the last 72 hours is £84.
The fastest flight from Boston to Chicago takes 2h 33m
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 24h 49m 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 £84. 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.


Choose the best way to get from Boston to Chicago

Buses

26h 01m
£81 one-way£154 return
Direct · from £154

Distance to city centre

ZUN0.7 mi
F990.8 mi

Find Buses

Boston to Chicago Buses

Trains

22h 15m
£78 one-way£157 return
Direct · from £157

Distance to city centre

ZUN0.7 mi

Find Trains

Boston to Chicago Trains

Flights

2h 33m
£51 one-way£84 return
Direct · from £841 stop · from £121

Distance to city centre

ORD15.9 mi

An easier way to manage your Chicago trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
From?
To?
Thu 2/5
Thu 9/5
Email me momondo's favourite deals

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