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Cheap flights from Boston to Chicago from £84

BOS — CHI
20 Nov — 27 Nov1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in January or February, booked 55 days in advance, depart on a Thursday or Saturday and return on a Friday

Cheap flight deals from Boston to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Boston to Chicago

Thu 3/1217:55 -
Nonstop2h 45m
Sun 6/1213:00 -
Nonstop2h 10m
Deal found 21/10£159
Mon 23/1120:40 -
Nonstop2h 56m
Fri 27/1107:05 -
Nonstop2h 27m
Deal found 20/10£159
Thu 3/1212:50 -
Nonstop2h 50m
Thu 10/1213:15 -
Nonstop2h 05m
Deal found 19/10£160
Mon 23/1115:41 -
1 stop7h 37m
Thu 26/1109:13 -
Nonstop2h 33m
Deal found 21/10£164
Thu 12/1109:00 -
1 stop5h 09m
Sun 15/1107:00 -
Nonstop2h 19m
Deal found 21/10£167
Thu 24/1205:45 -
Nonstop3h 06m
Tue 29/1221:49 -
Nonstop2h 29m
Deal found 21/10£169
Thu 3/1212:50 -
Nonstop2h 50m
Mon 7/1213:15 -
2 stops7h 40m
Deal found 19/10£171
Fri 25/1217:00 -
1 stop6h 15m
Thu 31/1216:00 -
Nonstop2h 29m
Deal found 21/10£173
Thu 12/1106:45 -
1 stop6h 14m
Tue 17/1109:30 -
1 stop5h 22m
Deal found 21/10£174
Thu 12/1109:15 -
1 stop5h 44m
Thu 19/1108:04 -
1 stop5h 52m
Deal found 21/10£174
Thu 3/1209:15 -
Nonstop3h 04m
Sun 6/1208:52 -
1 stop4h 40m
Deal found 20/10£175
Sat 19/1205:45 -
Nonstop3h 06m
Mon 21/1206:50 -
Nonstop2h 27m
Deal found 20/10£176

Find flight deals from Boston to Chicago

Round-trip from

£159

One-way from

£84

Popular in

October

Cheapest in

January

Average price

£246

Good one-way deal

£149 or less
Southwest
  • Southwest
  • 10/11-11/11
  • Nonstop
  • 5h 15m total
  • Boston to Chicago
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United Airlines
  • United Airlines
  • 9/11-31/12
  • 1 total stop
  • 7h 37m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 13% potential increase in price (£22 potential increase over avg. return price).
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Cheapest flight prices on average. 3% potential price decrease (£5 potential savings vs. average return price).
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Average for round-trip flights in October 2026
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Price to beat on a one-way flight from Boston Logan Intl to Chicago (CHI).
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Cheapflights Fare Finder

 
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

Cheapest return flight

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sat 21/11

19:10-00:25

1 stop6h 15m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£88

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sat 21/11

19:00-23:54

1 stop5h 54m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£88

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Tue 1/12

13:20-19:45

2 stops7h 25m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£91

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Fri 13/11

16:20-18:05

Nonstop2h 45m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£103

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 22/11

07:31-09:34

Nonstop3h 03m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£108

BostonChicago

BOS Boston Logan Intl - MDW Chicago Midway

BOSMDW

Boston Logan Intl

Sun 31/1

17:25-19:25

Nonstop3h 00m

Chicago Midway

Wed 31/12

00:00-01:00

Nonstop0h 00m

£115

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 21/3

20:42-22:47

Nonstop3h 05m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£126

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Tue 22/12

14:55-17:01

Nonstop3h 06m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£126

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 3/1

09:10-11:16

Nonstop3h 06m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£126

BostonChicago

BOS Boston Logan Intl - ORD Chicago O'Hare Intl

BOSORD

Boston Logan Intl

Sun 27/12

05:45-07:51

Nonstop3h 06m

Chicago O'Hare Intl

Wed 31/12

00:00-01:00

Nonstop0h 00m

£126

Flights are sorted by cheapest return flights first.

Deals found on 18/10

Showing 1-10 of 41 resultsSorted by cheapest first
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Best time to book a flight from Boston to Chicago

Have a flexible travel schedule? Discover the best time to fly to Chicago from Boston with our price prediction graph.
Estimated return price

Cheapflights Insights

Everything you need to know about your flight from Boston to Chicago

What is the cheapest month to book a flight from Boston to Chicago?

Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £147). Flying from Boston to Chicago in October is currently the most expensive (average of £249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from BOS to CHI?

When flying from Boston to Chicago, the time of day you fly usually plays a role in the price. Save by searching for a flight in the evening, which can drop the price by up to 70% versus a flight at midday.

Weekly flight availability from Boston to Chicago

The most flights from BOS to CHI are scheduled on a Tuesday (71 on average). You will have fewer flight options on Sunday, which is when the least amount of flights are scheduled (10 on average).

How much does it cost for a return flight from Boston to Chicago?

Airfare is below average for this route at the moment.
Boston to Chicago flights typically cost between £161 and £292 in December.
The cheapest return price found within the last 5 days was £159 on Southwest (3 Dec–6 Dec).

How often are flights from Boston to Chicago delayed?

About 15% of weekly flights between Boston and Chicago have experienced delays in the past year, with the average delay time being 172 minutes.

What is the most punctual flight time for Boston to Chicago flights?

Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.

What day of the week experiences the fewest flight delays on this route?

Wednesday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.

Which airline has the best punctuality record on Boston to Chicago flights?

Over the past year, United Airlines have had the lowest number of delays on this route, with just 9% of flights being delayed.

How far ahead should I book a flight from Boston to Chicago?

The best time to book flights from Boston to Chicago is 59 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

Reviews of airlines servicing Chicago

Get a feel of what it's like to fly with American Airlines from Boston to Chicago by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
American Airlines
7.0
Good
12,178 reviews
Check prices

Food

6.4

Overall

7.0

Crew

7.9

Boarding

7.4

Entertainment

6.8

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.
American Airlines
7.0
Good
12,178 reviews
American Airlines
7.0
Good
12,178 reviews
Check prices

Food

6.4

Overall

7.0

Crew

7.9

Boarding

7.4

Entertainment

6.8

Comfort

7.1

Reviews

1 / 20
2.0
Mediocre

Anonymous,Aug 2025

BNA - ORD

My flight was 8 hours delayed, so I missed my connecting flight to Dublin. I understand it’s not the staff’s fault but the lack of sympathy and apology was appalling. I had been sat in the airport since 4am until 3pm and they did not seem understanding. Not good. Need better customer service.

Related info for your journey

  • What airport do you fly from for flights from Boston to Chicago?

    Boston Logan Intl (BOS) is the airport you will fly out of if you book a flight from Boston to Chicago. You should not have trouble finding flights to Chicago from Logan Intl; the airport handles an average of 50 outbound flights to Chicago per day. You should also have plenty of airline options to choose from since 0 airlines have flights from the Boston airport to Chicago. It is only a 2.6 mi journey to Logan Intl (BOS) from Boston’s city center.

  • How long is the flight from Boston to Chicago?

    A quick flight from Boston to Chicago can take about 2h 45m. Southwest provides one of the quickest options available for as low as £159. Airlines will cover a distance of 857 mi. This flight may include one or multiple stops.

  • What are the most reliable airlines from Boston to Chicago?

    No one likes to see their flight delayed. When booking a flight from Boston to Chicago consider choosing Japan Airlines (85%), Republic Airways (83%) or Cathay Pacific (79%) as they are the most reliable in getting you off to your destination on time.

  • Can I find deals for flights from Boston to Chicago that include hotel bookings?

    Yes. In addition to deals on Boston to Chicago flights, Cheapflights offers holiday packages that include both flights and hotel.

  • How can I find direct flights from Boston to Chicago?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Chicago.

  • Can I find deals for business class flights from Boston to Chicago?

    Yes. Cheapflights offers flight deals from Boston to Chicago by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Boston to Chicago?

    Currently, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £147). Flying from Boston to Chicago in October is currently the most expensive (average of £249). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

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Alternative routes for Boston to Chicago

Boston to O'Hare Intl flights

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