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Cheap flights from Boston to Chicago from £59

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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
3 Apr — 10 Apr1
1 adult

Cheapflights Tip: The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 49 days in advance, depart on a Friday or Thursday 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 29 March 2025.

Round-trip from

£111

One-way from

£59

Popular in

May

Cheapest in

September

Average price

£214

Good round-trip deal

£76 or less

Good one-way deal

£77 or less
United Airlines
  • United Airlines
  • 28/8-1/9
  • 1 total stop
  • 7h 38m total
  • Boston to Chicago
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United Airlines
  • United Airlines
  • 3/7
  • Nonstop
  • 2h 58m total
  • Boston to Chicago
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Highest demand for flights based on searches. 11% potential increase in price (£18 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£3 potential savings vs. average return price).
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Average for round-trip flights in March 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 29 March 2025.

Thu 28/819:30BOS - ORD
1 stop5h 12mUnited Airlines
Mon 1/906:30ORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 28/3£111
Tue 6/506:00BOS - ORD
Nonstop3h 00mJetBlue
Wed 7/506:15ORD - BOS
1 stop4h 27mJetBlue
Deal found 29/3£114
Sat 24/517:10BOS - ORD
Nonstop3h 04mDelta
Wed 28/518:30ORD - BOS
Nonstop2h 33mDelta
Deal found 29/3£121
Mon 7/405:50BOS - ORD
1 stop9h 10mSouthwest
Thu 10/416:00ORD - BOS
1 stop5h 35mSouthwest
Deal found 28/3£136
Sun 13/405:00BOS - ORD
Nonstop3h 00mAmerican Airlines
Tue 15/407:00ORD - BOS
1 stop7h 26mAmerican Airlines
Deal found 27/3£182
Sun 4/521:05BOS - ORD
2 stops28h 16mSpirit Airlines
Sun 11/516:35ORD - BOS
3 stops29h 16mSpirit Airlines
Deal found 28/3£209
Sat 19/406:30BOS - ORD
1 stop15h 24mSun Country Air
Thu 24/419:15ORD - BOS
1 stop14h 20mSun Country Air
Deal found 28/3£220

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 29 March 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

Thu 28/8

19:30-23:42

1 stop5h 12m

Chicago O'Hare Intl

Mon 1/9

06:30-09:56

Nonstop2h 26m

£111

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 6/5

16:30-18:36

Nonstop3h 06m

Chicago O'Hare Intl

Thu 8/5

06:15-15:01

1 stop7h 46m

£114

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 24/5

17:10-19:14

Nonstop3h 04m

Chicago O'Hare Intl

Wed 28/5

18:30-22:03

Nonstop2h 33m

£121

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 27/4

06:40-16:45

1 stop11h 05m

Chicago O'Hare Intl

Thu 1/5

13:50-21:00

1 stop6h 10m

£136

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 13/4

05:00-07:00

Nonstop3h 00m

Chicago O'Hare Intl

Tue 15/4

07:00-15:26

1 stop7h 26m

£182

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 4/5

21:05-00:21

2 stops28h 16m

Chicago O'Hare Intl

Sun 11/5

16:35-22:51

3 stops29h 16m

£209

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 19/4

06:30-20:54

1 stop15h 24m

Chicago O'Hare Intl

Thu 24/4

19:15-10:35

1 stop14h 20m

£220

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/7

07:45-09:43

Nonstop2h 58m

£59

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 5/5

20:10-22:06

Nonstop2h 56m

£61

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 18/5

06:00-08:00

Nonstop3h 00m

£65

Flights are sorted by cheapest return flights first.

Deals found on 28/3

Showing 1-10 of 15 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 21 March 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 29 March 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 65% 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 29 March 2025.

The most flights from BOS to CHI are scheduled on a Friday (61 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (9 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 29 March 2025.
Read reviews from past customers who have flown Southwest, Alaska Airlines 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.
Southwest
8.1
Very Good
4,273 reviews
Check prices

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very Good
4,273 reviews
Southwest
8.1
Very Good
4,273 reviews
Check prices

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Alaska Airlines
8.0
Very Good
9,797 reviews
Southwest
8.1
Very Good
4,273 reviews
Check prices

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very Good
7,895 reviews
Southwest
8.1
Very Good
4,273 reviews
Check prices

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,609 reviews
Southwest
8.1
Very Good
4,273 reviews
Check prices

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,922 reviews
Southwest
8.1
Very Good
4,273 reviews
Check prices

Overall

8.1

Boarding

8.2

Comfort

8.1

Crew

8.7

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

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 28 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 £111, United Airlines will fly you from Boston to Chicago and back. In addition to United Airlines, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from JetBlue and Delta - these airlines can fly you to your destination from £114 and £121, respectively. These flights start at 40% 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 £59. However, be on the lookout for offers from Delta 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 WestJet (96%), Avianca (89%) or Virgin Atlantic (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 £76. On average you can expect to pay £88. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £129.

  • 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

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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