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Cheap flights from Boston to Chicago from £48

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 30/6. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
23 Apr — 30 Apr1
1 adult

Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 90 days in advance, depart on a Thursday or Wednesday and return on a Wednesday

Cheap 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 18 April 2025.

Round-trip from

£96

One-way from

£48

Popular in

May

Cheapest in

September

Average price

£203

Good round-trip deal

£383 or less

Good one-way deal

£44 or less
JetBlue
  • JetBlue
  • 4/5-6/5
  • 1 total stop
  • 10h 51m total
  • Boston to Chicago
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United Airlines
  • United Airlines
  • 30/6
  • 1 total stop
  • 5h 38m total
  • Boston to Chicago
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Highest demand for flights based on searches. 9% potential increase in price (£14 potential increase over avg. return price).
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Cheapest flight prices on average. 1% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in April 2025
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Price to beat on a round-trip flight from Boston Logan Intl to Chicago (CHI).
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Price to beat on a one-way flight from Boston Logan Intl to Chicago (CHI).
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Find flight deals from Boston to Chicago

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 18 April 2025.

Sun 4/506:00BOS - ORD
Nonstop3h 05mJetBlue
Tue 6/506:15ORD - BOS
1 stop7h 46mJetBlue
Deal found 17/4£96
Fri 2/505:30BOS - ORD
1 stop7h 20mSouthwest
Wed 7/513:50ORD - BOS
1 stop4h 20mSouthwest
Deal found 17/4£103
Wed 25/606:00BOS - ORD
Nonstop2h 58mUnited Airlines
Sun 29/621:32ORD - BOS
Nonstop2h 27mUnited Airlines
Deal found 17/4£104
Fri 9/520:20BOS - ORD
Nonstop2h 54mDelta
Sun 11/507:00ORD - BOS
Nonstop2h 25mDelta
Deal found 17/4£136
Wed 25/605:00BOS - ORD
Nonstop2h 54mAmerican Airlines
Sun 29/605:00ORD - BOS
1 stop4h 15mAmerican Airlines
Deal found 16/4£140
Thu 30/1011:45BOS - ORD
1 stop7h 41mSun Country Air
Sun 2/1111:42ORD - BOS
1 stop21h 59mSun Country Air
Deal found 17/4£245
Wed 23/419:59BOS - ORD
1 stop13h 05mMultiple Airlines
Thu 24/419:15ORD - BOS
1 stop14h 20mMultiple Airlines
Deal found 17/4£254

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 18 April 2025.
Use the filters below to find and compare flights from Boston to Chicago that are best for you.

Fly from

Boston

Fly to

Chicago

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 4/5

06:00-08:05

Nonstop3h 05m

Chicago O'Hare Intl

Tue 6/5

06:15-15:01

1 stop7h 46m

£96

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 2/5

05:30-11:50

1 stop7h 20m

Chicago O'Hare Intl

Wed 7/5

13:50-19:10

1 stop4h 20m

£103

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 25/6

06:00-07:58

Nonstop2h 58m

Chicago O'Hare Intl

Sun 29/6

21:32-00:59

Nonstop2h 27m

£104

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 9/5

20:20-22:14

Nonstop2h 54m

Chicago O'Hare Intl

Sun 11/5

07:00-10:25

Nonstop2h 25m

£136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 25/6

05:00-06:54

Nonstop2h 54m

Chicago O'Hare Intl

Sun 29/6

05:00-10:15

1 stop4h 15m

£140

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 30/6

18:59-23:37

1 stop5h 38m

£48

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 1/5

05:30-11:50

1 stop7h 20m

£51

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 30/4

05:10-12:13

1 stop8h 03m

£52

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 28/4

20:59-22:57

Nonstop2h 58m

£71

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 24/4

21:39-08:04

1 stop11h 25m

£72

Flights are sorted by cheapest return flights first.

Deals found on 17/4

Showing 1-10 of 13 results
1
2

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 11 April 2025.

The best time to book flights from Boston to Chicago is 49 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, January is the cheapest month in which you can book a flight from Boston to Chicago (average of £595). Flying from Boston to Chicago in July is currently the most expensive (average of £843). 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 18 April 2025.

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 morning, which can drop the price by up to 69% versus a flight at midday.

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 18 April 2025.

The most flights from BOS to CHI are scheduled on a Thursday (66 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (14 on average).

Rainfall in Chicago by month

Plan your trip to Chicago by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Chicago ranges from 43.0 - 125.0 inches per month. August is typically the wettest month, when rainfall can reach 125.0 mm. January is typically the driest time to visit Chicago when rainfall is around 43.0 mm.

Temperature in Chicago by month

Plan your trip to Chicago by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Chicago, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 23.0 C. Travellers hoping to avoid the cold should look outside of January, when temperatures are typically at their lowest (around -5.0 C).

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 18 April 2025.
Read reviews from past customers who have flown Alaska Airlines, Southwest and Delta from Boston to Chicago. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Alaska Airlines
8.0
Very Good
9,887 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Southwest
8.0
Very Good
4,280 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
Delta
8.0
Very Good
7,917 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
United Airlines
7.4
Good
8,667 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >
JetBlue
7.3
Good
2,928 reviews
Alaska Airlines
8.0
Very Good
9,887 reviews
Check prices

Crew

8.5

Boarding

8.1

Overall

8.0

Entertainment

7.1

Food

7.1

Comfort

7.9

Reviews

1 / 20
4.0
Okay

Anonymous,Apr 2025

LAS - STS

flight was delayed both ways even tho the weather was clear >

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 40 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.

  • What are the cheapest airlines flying from Boston to Chicago round-trip?

    Currently priced at £96, JetBlue will fly you from Boston to Chicago and back. In addition to JetBlue, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Southwest and United Airlines - these airlines can fly you to your destination from £103 and £104, respectively. These flights start at 46% lower than the current average price 3 months from now.

  • What are the cheapest airlines to fly from Boston to Chicago one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as £48. However, be on the lookout for offers from Southwest and JetBlue, as they are both options that can get you from Boston to Chicago for a low price.

  • 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 Avianca (91%), ANA (89%) or United Airlines (87%) 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 £44. On average you can expect to pay £244. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £115.

  • 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 £595). Flying from Boston to Chicago in July is currently the most expensive (average of £843). 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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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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