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Cheap flights from Boston to Chicago from £56

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 19/5. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
22 May — 29 May1
1 adult
1 adult, Economy, 0 bags
Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 78 days in advance, depart on a Thursday or Saturday 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 22 April 2026.

Thu 28/507:35
BOS
-
ORD
Nonstop2h 52m
Delta
Fri 29/519:16
ORD
-
BOS
Nonstop2h 34m
Delta
Deal found 20/4£111
Tue 12/518:47
BOS
-
ORD
Nonstop3h 06m
JetBlue
Tue 26/520:30
ORD
-
BOS
Nonstop2h 29m
JetBlue
Deal found 21/4£112
Wed 20/508:05
BOS
-
ORD
Nonstop3h 01m
United Airlines
Mon 25/506:15
ORD
-
BOS
Nonstop2h 24m
United Airlines
Deal found 20/4£115
Tue 12/509:05
BOS
-
ORD
1 stop4h 56m
Delta
Tue 12/517:19
ORD
-
BOS
1 stop5h 10m
Delta
Deal found 20/4£116
Sat 30/506:00
BOS
-
ORD
1 stop7h 16m
Delta
Mon 1/617:19
ORD
-
BOS
1 stop5h 10m
Delta
Deal found 20/4£117
Thu 28/505:51
BOS
-
ORD
1 stop6h 56m
Delta
Mon 1/617:19
ORD
-
BOS
1 stop5h 10m
Delta
Deal found 20/4£118
Fri 28/807:30
BOS
-
ORD
Nonstop2h 58m
Delta
Mon 31/817:45
ORD
-
BOS
1 stop4h 47m
Delta
Deal found 20/4£118
Sat 9/506:00
BOS
-
ORD
Nonstop3h 00m
United Airlines
Tue 12/507:30
ORD
-
BOS
Nonstop2h 31m
United Airlines
Deal found 21/4£119
Sat 9/517:30
BOS
-
ORD
Nonstop3h 03m
Delta
Tue 12/510:30
ORD
-
BOS
Nonstop2h 27m
Delta
Deal found 20/4£120
Sat 9/512:00
BOS
-
ORD
Nonstop2h 54m
Delta
Mon 11/507:00
ORD
-
BOS
Nonstop2h 35m
Delta
Deal found 20/4£121
Fri 15/518:39
BOS
-
ORD
Nonstop3h 01m
United Airlines
Tue 19/513:55
ORD
-
BOS
Nonstop2h 27m
United Airlines
Deal found 22/4£121
Fri 8/518:47
BOS
-
ORD
Nonstop3h 06m
JetBlue
Wed 13/509:49
ORD
-
BOS
Nonstop2h 31m
JetBlue
Deal found 21/4£123

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 22 April 2026.

Round-trip from

£111

One-way from

£56

Popular in

April

Cheapest in

September

Average price

£192

Good round-trip deal

£138 or less

Good one-way deal

£130 or less
Delta
  • Delta
  • 28/5-29/5
  • Nonstop
  • 5h 26m total
  • Boston to Chicago
Search Deals
Frontier
  • Frontier
  • 19/5
  • 1 total stop
  • 11h 20m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 9% potential increase in price (£13 potential increase over avg. return price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease (£2 potential savings vs. average return price).
Search Deals
Average for round-trip flights in April 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).
Search Deals

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 22 April 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

Thu 28/5

05:51-11:47

1 stop6h 56m

Chicago O'Hare Intl

Tue 2/6

07:05-14:15

1 stop6h 10m

£117

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 30/5

17:30-19:33

Nonstop3h 03m

Chicago O'Hare Intl

Wed 10/6

19:25-23:02

Nonstop2h 37m

£124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 19/5

05:45-09:37

1 stop4h 52m

Chicago O'Hare Intl

Sat 23/5

15:55-19:30

Nonstop2h 35m

£131
Fastest return journey

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 25/9

20:10-22:06

Nonstop2h 56m

Chicago O'Hare Intl

Mon 28/9

07:00-10:28

Nonstop2h 28m

£132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 4/6

07:35-09:27

Nonstop2h 52m

Chicago O'Hare Intl

Wed 10/6

17:22-23:54

1 stop5h 32m

£138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 6/6

07:35-09:39

Nonstop3h 04m

Chicago O'Hare Intl

Tue 9/6

06:00-12:23

1 stop5h 23m

£138

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 19/7

07:56-09:53

Nonstop2h 57m

Chicago O'Hare Intl

Wed 22/7

20:20-23:51

Nonstop2h 31m

£142

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 11/5

18:30-22:43

1 stop5h 13m

Chicago O'Hare Intl

Wed 13/5

18:50-22:27

Nonstop2h 37m

£159

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 27/8

20:10-22:06

Nonstop2h 56m

Chicago O'Hare Intl

Sun 30/8

07:00-13:24

1 stop5h 24m

£182

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 6/7

20:45-22:42

Nonstop2h 57m

Chicago O'Hare Intl

Sat 11/7

16:30-20:11

Nonstop2h 41m

£183

Flights are sorted by cheapest return flights first.

Deals found on 21/4

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

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

Use this chart to determine the optimal time to book a return flight from Boston to Chicago. Price data was last updated on 17 April 2026.

The best time to book flights from Boston to Chicago is 78 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.

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 £123). Flying from Boston to Chicago in April 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 22 April 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 69% versus a flight in the morning.

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 22 April 2026.

The most flights from BOS to CHI are scheduled on a Monday (65 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (30 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 172 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?

Saturday 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 10% of flights being delayed.

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 22 April 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
11,647 reviews
Check prices

Comfort

7.2

Boarding

7.5

Food

6.4

Crew

7.9

Entertainment

6.9

Overall

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
7.1
Good
11,647 reviews
American Airlines
7.1
Good
11,647 reviews
Check prices

Comfort

7.2

Boarding

7.5

Food

6.4

Crew

7.9

Entertainment

6.9

Overall

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

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 47 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 4h 52m. Delta provides one of the quickest options available for as low as £131. 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 ANA (81%), Envoy Air (80%) or United Airlines (77%) 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 £102. On average you can expect to pay £163. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £131.

  • 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 £123). Flying from Boston to Chicago in April 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

See prices for flight routes from nearby airports that may be better suited for you.
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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