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Cheap flights from Boston to Chicago from £73

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 28/8. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
5 Aug — 12 Aug1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in January or September, booked 90 days in advance, depart on a Saturday or Thursday and return on a Saturday

Cheap flight deals from Boston to Chicago

Enter your travel dates to find the best prices.

Cheapest flights from Boston to Chicago
Explore the most affordable flight options available from Boston to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on 6 July 2026.

Sat 18/718:43
BOS
-
ORD
Nonstop2h 57m
United Airlines
Sat 25/718:20
ORD
-
BOS
Nonstop2h 36m
United Airlines
Deal found 1/7£127
Tue 28/707:19
BOS
-
ORD
Nonstop2h 58m
United Airlines
Wed 29/706:00
ORD
-
BOS
1 stop4h 16m
United Airlines
Deal found 3/7£129
Sat 25/720:20
BOS
-
ORD
Nonstop3h 00m
United Airlines
Sat 19/915:35
ORD
-
BOS
Nonstop2h 44m
United Airlines
Deal found 3/7£129
Wed 12/808:15
BOS
-
ORD
Nonstop2h 56m
JetBlue
Thu 20/809:35
ORD
-
BOS
1 stop6h 32m
JetBlue
Deal found 2/7£131
Sat 22/811:05
BOS
-
ORD
Nonstop2h 54m
JetBlue
Mon 24/806:00
ORD
-
BOS
1 stop7h 43m
JetBlue
Deal found 3/7£132
Tue 21/716:15
BOS
-
ORD
Nonstop3h 04m
Delta
Thu 6/819:30
ORD
-
BOS
Nonstop2h 30m
Delta
Deal found 2/7£133
Mon 20/707:19
BOS
-
ORD
Nonstop2h 58m
United Airlines
Wed 22/719:45
ORD
-
BOS
Nonstop2h 36m
United Airlines
Deal found 1/7£134
Mon 27/706:00
BOS
-
ORD
Nonstop2h 58m
United Airlines
Wed 29/706:00
ORD
-
BOS
1 stop4h 16m
United Airlines
Deal found 2/7£135
Mon 31/807:30
BOS
-
ORD
Nonstop2h 56m
Delta
Sat 12/911:30
ORD
-
BOS
Nonstop2h 45m
Delta
Deal found 3/7£135
Wed 22/717:10
BOS
-
ORD
Nonstop3h 05m
JetBlue
Sat 25/713:09
ORD
-
BOS
Nonstop2h 34m
JetBlue
Deal found 1/7£136
Mon 10/805:01
BOS
-
ORD
1 stop4h 51m
JetBlue
Thu 20/820:20
ORD
-
BOS
Nonstop2h 31m
JetBlue
Deal found 2/7£137

Find flight deals from Boston to Chicago

Discover tips and strategies to find the most affordable flight options for your journey from Boston (BOS) to Chicago (CHI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated 6 July 2026.

Round-trip from

£127

One-way from

£73

Popular in

June

Cheapest in

January

Average price

£180

Good round-trip deal

£228 or less

Good one-way deal

£100 or less
United Airlines
  • United Airlines
  • 18/7-25/7
  • Nonstop
  • 5h 33m total
  • Boston to Chicago
Search Deals
United Airlines
  • United Airlines
  • 22/8
  • 1 total stop
  • 5h 15m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 7% potential increase in price (£10 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
Search Deals
Average for round-trip flights in July 2026
Search Deals
Price to beat on a round-trip flight from Boston Logan Intl to Chicago (CHI).
Search Deals
Price to beat on a one-way flight from Boston Logan Intl to Chicago (CHI).
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Cheapflights 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, Cheapflights users made 858,174 searches. Data last updated 6 July 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

Cheapest return flight

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 5/8

08:15-10:12

Nonstop2h 57m

Chicago O'Hare Intl

Tue 11/8

06:00-11:17

1 stop4h 17m

£129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 22/7

05:45-09:36

1 stop4h 51m

Chicago O'Hare Intl

Sat 25/7

19:45-23:21

Nonstop2h 36m

£129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 20/8

05:45-09:38

1 stop4h 53m

Chicago O'Hare Intl

Sat 22/8

06:15-09:36

Nonstop2h 21m

£129

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 18/8

17:21-19:27

Nonstop3h 06m

Chicago O'Hare Intl

Tue 25/8

09:40-18:57

1 stop8h 17m

£131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 1/9

17:20-19:26

Nonstop3h 06m

Chicago O'Hare Intl

Sat 5/9

17:27-23:59

1 stop5h 32m

£131

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 28/7

05:45-09:36

1 stop4h 51m

Chicago O'Hare Intl

Thu 30/7

21:41-01:14

Nonstop2h 33m

£135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 2/8

20:30-22:30

Nonstop3h 00m

Chicago O'Hare Intl

Tue 4/8

06:00-11:16

1 stop4h 16m

£135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 31/8

07:30-09:26

Nonstop2h 56m

Chicago O'Hare Intl

Sat 12/9

11:30-15:15

Nonstop2h 45m

£135

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 22/8

16:43-21:58

1 stop6h 15m

Chicago O'Hare Intl

Mon 24/8

20:20-23:51

Nonstop2h 31m

£138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/9

05:45-09:38

1 stop4h 53m

Chicago O'Hare Intl

Thu 3/9

21:40-01:11

Nonstop2h 31m

£138

Flights are sorted by cheapest return flights first.

Deals found on 4/7

Showing 1-10 of 23 resultsSorted by cheapest first
1
2
3

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
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

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, September is the cheapest month in which you can book a flight from Boston to Chicago (average of £125). Flying from Boston to Chicago in July is currently the most expensive (average of £219). 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?

Find hourly flight availability from Boston to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated 6 July 2026.

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 64% versus a flight in the afternoon.

Weekly flight availability from Boston to Chicago

Explore weekly flight availability from Boston to Chicago. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated 6 July 2026.

The most flights from BOS to CHI are scheduled on a Sunday (79 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (35 on average).

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

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 173 minutes.

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

Historically, flights departing in the morning 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 Sunday 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 11% 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 77 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 insights into the airlines that provide service to Chicago. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Chicago. Reviews last updated 6 July 2026.
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
7.1
Good
11,782 reviews
Check prices

Overall

7.1

Comfort

7.2

Food

6.4

Crew

7.9

Boarding

7.5

Entertainment

6.8

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
7.1
Good
11,782 reviews
American Airlines
7.1
Good
11,782 reviews
Check prices

Overall

7.1

Comfort

7.2

Food

6.4

Crew

7.9

Boarding

7.5

Entertainment

6.8

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

Find useful and relevant information for your journey from Boston to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • 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 53 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 56m. United Airlines provides one of the quickest options available for as low as £135. Airlines will cover a distance of 864 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 (93%), Cathay Pacific (89%) or Royal Jordanian (86%) as they are the most reliable in getting you off to your destination on time.

  • What are the cheapest flights from Boston to Chicago?

    The cheapest flight price from Boston to Chicago is £59. On average you can expect to pay £256. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £150.

  • 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, September is the cheapest month in which you can book a flight from Boston to Chicago (average of £125). Flying from Boston to Chicago in July is currently the most expensive (average of £219). 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

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Boston to O'Hare Intl flights

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Users can book flights with no change fees policies with our dedicated filters. Book flights from Boston to Chicago flexibly with Cheapflights today.

Can Cheapflights notify me if prices for flights from Boston to Chicago become cheaper?

Yes, Cheapflights has a feature called Price Alert, which notifies users when flight prices change. Track prices for your flight to Chicago from Boston today and book when prices fit your budget.

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