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Cheap flights from Boston to Chicago from £63

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 24/3. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
26 Feb — 5 Mar1
1 adult

The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 76 days in advance, depart on a Wednesday or Friday 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 21 February 2025.

Round-trip from

£123

One-way from

£63

Popular in

April

Cheapest in

September

Average price

£203

Good one-way deal

£105 or less
Frontier
  • Frontier
  • 6/3-9/3
  • 2 total stops
  • 30h 41m total
  • Boston to Chicago
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JetBlue
  • JetBlue
  • 24/3
  • Nonstop
  • 3h 00m total
  • Boston to Chicago
Search Deals
Highest demand for flights based on searches. 14% potential increase in price (£25 potential increase over avg. return price).
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Cheapest flight prices on average. 2% potential price decrease (£4 potential savings vs. average return price).
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Average for round-trip flights in February 2025
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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 21 February 2025.

Thu 6/305:10BOS - ORD
1 stop6h 40mFrontier
Sun 9/308:10ORD - BOS
1 stop24h 01mFrontier
Deal found 20/2£123
Thu 27/207:15BOS - ORD
Nonstop3h 06mDelta
Mon 10/318:55ORD - BOS
Nonstop2h 22mDelta
Deal found 20/2£124
Tue 1/422:47BOS - ORD
3 stops31h 59mSpirit Airlines
Tue 15/411:53ORD - BOS
2 stops26h 28mSpirit Airlines
Deal found 20/2£126
Fri 28/206:00BOS - ORD
Nonstop3h 04mUnited Airlines
Mon 3/309:15ORD - BOS
Nonstop2h 23mUnited Airlines
Deal found 20/2£128
Mon 10/314:30BOS - ORD
Nonstop3h 00mJetBlue
Thu 13/313:15ORD - BOS
Nonstop2h 24mJetBlue
Deal found 20/2£132
Thu 6/306:59BOS - ORD
Nonstop3h 05mAmerican Airlines
Sun 9/310:28ORD - BOS
1 stop5h 35mAmerican Airlines
Deal found 20/2£164
Mon 10/305:35BOS - ORD
2 stops8h 10mSouthwest
Wed 12/316:00ORD - BOS
1 stop6h 00mSouthwest
Deal found 20/2£190

Find flights from Boston to Chicago within your budget

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 21 February 2025.

Fly from

Boston

Fly to

Chicago

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/3

05:10-10:50

1 stop6h 40m

Chicago O'Hare Intl

Sun 9/3

08:10-09:11

1 stop24h 01m

£123

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 9/3

07:00-09:09

Nonstop3h 09m

Chicago O'Hare Intl

Tue 25/3

10:55-14:12

Nonstop2h 17m

£124

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 3/4

07:43-09:40

Nonstop2h 57m

Chicago O'Hare Intl

Mon 14/4

21:30-00:58

Nonstop2h 28m

£125

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 1/4

22:47-05:46

3 stops31h 59m

Chicago O'Hare Intl

Tue 15/4

11:53-15:21

2 stops26h 28m

£126

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 10/3

05:20-10:59

1 stop6h 39m

Chicago O'Hare Intl

Thu 27/3

13:00-16:20

Nonstop2h 20m

£132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/3

06:59-09:04

Nonstop3h 05m

Chicago O'Hare Intl

Sun 9/3

10:28-17:03

1 stop5h 35m

£164

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 10/3

05:35-12:45

2 stops8h 10m

Chicago O'Hare Intl

Wed 12/3

16:00-23:00

1 stop6h 00m

£190

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 24/3

14:30-16:30

Nonstop3h 00m

£63

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 31/5

06:00-07:58

Nonstop2h 58m

£66

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sun 27/4

06:40-14:05

1 stop8h 25m

£86

Flights are sorted by cheapest return flights first.

Deals found on 21/2

Showing 1-10 of 14 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.

Travel insights for flights from Boston to Chicago

Get recent, data-driven insights about flights from Boston to Chicago including ideal travel times, pricing trends, and more.

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 14 February 2025.

The best time to book flights from Boston to Chicago is 76 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 21 February 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 58% 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 21 February 2025.

The most flights from BOS to CHI are scheduled on a Thursday (56 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (11 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 21 February 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
4,401 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Southwest
8.1
Very Good
4,401 reviews
Southwest
8.1
Very Good
4,401 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Alaska Airlines
8.0
Very Good
9,697 reviews
Southwest
8.1
Very Good
4,401 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

Delta
8.0
Very Good
8,213 reviews
Southwest
8.1
Very Good
4,401 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

JetBlue
7.4
Good
3,069 reviews
Southwest
8.1
Very Good
4,401 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

United Airlines
7.4
Good
8,759 reviews
Southwest
8.1
Very Good
4,401 reviews
Check prices

Crew

8.7

Boarding

8.2

Comfort

8.1

Food

7.1

Overall

8.1

Entertainment

7.6

Reviews

1 / 20

2.0
Mediocre

Anonymous,Feb 2025

MCO - STL

Cancelled at last minute, SWA unable to assist in formulating alternate plans. Wound up renting a car and driving 13 hours to beat bad weather forecast at home. Not SWA’s fault that there was significant bad weather across the country.

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 41 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 £123, Frontier will fly you from Boston to Chicago and back. In addition to Frontier, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from Delta and United Airlines - these airlines can fly you to your destination from £124 and £125, respectively. These flights start at 37% 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 JetBlue, with whom users have recently found tickets for as low as £63. However, be on the lookout for offers from United Airlines and Southwest, 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 Air France (100%), Japan Airlines (90%) or KLM (90%) 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 £62. On average you can expect to pay £270. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £205.

  • 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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