Find flights
Deals
When to book
Airlines
FAQs

Cheap flights from Boston to Chicago from £65

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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
22 Jan — 29 Jan1
1 adult

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 17 January 2025.

Round-trip from

£120

One-way from

£65

Popular in

April

Cheapest in

September

Average price

£156
Frontier
  • Frontier
  • 15/4-16/4
  • 2 total stops
  • 21h 08m total
  • Boston to Chicago
Search Deals
United Airlines
  • United Airlines
  • 7/2
  • Nonstop
  • 2h 58m total
  • Boston to Chicago
Search Deals
High demand for flights, 14% potential price rise
Search Deals
Best time to find cheap flights, 2% potential price drop
Search Deals
Average for round-trip flights in January 2025
Search Deals

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 17 January 2025.

Tue 15/407:00BOS - ORD
1 stop10h 52mMultiple Airlines
Wed 16/413:14ORD - BOS
1 stop10h 16mMultiple Airlines
Deal found 16/1£120
Tue 4/210:00BOS - ORD
1 stop7h 10mSpirit Airlines
Wed 12/205:15ORD - BOS
2 stops14h 49mSpirit Airlines
Deal found 17/1£125
Sat 8/215:52BOS - ORD
Nonstop3h 03mJetBlue
Tue 11/207:00ORD - BOS
Nonstop2h 15mJetBlue
Deal found 16/1£128
Mon 14/405:10BOS - ORD
1 stop12h 16mFrontier
Sat 19/416:59ORD - BOS
1 stop14h 17mFrontier
Deal found 16/1£132
Wed 12/207:15BOS - ORD
Nonstop3h 06mDelta
Mon 17/207:10ORD - BOS
Nonstop2h 33mDelta
Deal found 17/1£146
Mon 10/316:17BOS - ORD
1 stop6h 43mUnited Airlines
Thu 13/321:30ORD - BOS
Nonstop2h 20mUnited Airlines
Deal found 16/1£150
Tue 4/209:26BOS - ORD
1 stop5h 49mAmerican Airlines
Wed 12/206:30ORD - BOS
Nonstop2h 33mAmerican Airlines
Deal found 17/1£170
Wed 26/206:05BOS - ORD
2 stops11h 40mSouthwest
Wed 5/315:10ORD - BOS
1 stop6h 00mSouthwest
Deal found 16/1£214
Thu 17/411:31BOS - ORD
1 stop7h 42mSun Country Air
Mon 21/419:05ORD - BOS
1 stop14h 30mSun Country Air
Deal found 16/1£233

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 17 January 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 15/4

07:00-16:52

1 stop10h 52m

Chicago O'Hare Intl

Wed 16/4

13:14-00:30

1 stop10h 16m

£120

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 8/2

15:52-17:55

Nonstop3h 03m

Chicago O'Hare Intl

Tue 11/2

07:00-10:15

Nonstop2h 15m

£128

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 14/4

05:10-16:26

1 stop12h 16m

Chicago O'Hare Intl

Sat 19/4

16:59-08:16

1 stop14h 17m

£132

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/2

10:00-16:10

1 stop7h 10m

Chicago O'Hare Intl

Wed 12/2

05:15-21:04

2 stops14h 49m

£133

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 10/3

16:17-22:00

1 stop6h 43m

Chicago O'Hare Intl

Thu 13/3

21:30-00:50

Nonstop2h 20m

£150

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 24/2

20:20-22:19

Nonstop2h 59m

Chicago O'Hare Intl

Thu 6/3

07:10-10:43

Nonstop2h 33m

£154

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 4/2

10:49-15:04

1 stop5h 15m

Chicago O'Hare Intl

Wed 12/2

12:30-15:49

Nonstop2h 19m

£170

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 26/2

06:05-16:45

2 stops11h 40m

Chicago O'Hare Intl

Wed 5/3

15:10-22:10

1 stop6h 00m

£214

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 17/4

11:31-18:13

1 stop7h 42m

Chicago O'Hare Intl

Mon 21/4

19:05-10:35

1 stop14h 30m

£233

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 7/2

12:12-14:10

Nonstop2h 58m

£65

Flights are sorted by cheapest return flights first.

Deals found on 16/1

Showing 1-10 of 17 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 10 January 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 17 January 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 23% 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 17 January 2025.

The most flights from BOS to CHI are scheduled on a Thursday (52 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (13 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 17 January 2025.
Read reviews from past customers who have flown JetBlue, Delta and United Airlines 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
4,659 reviews
Check prices

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very Good
4,659 reviews
Southwest
8.1
Very Good
4,659 reviews
Check prices

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very Good
9,684 reviews
Southwest
8.1
Very Good
4,659 reviews
Check prices

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very Good
8,513 reviews
Southwest
8.1
Very Good
4,659 reviews
Check prices

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,199 reviews
Southwest
8.1
Very Good
4,659 reviews
Check prices

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,969 reviews
Southwest
8.1
Very Good
4,659 reviews
Check prices

Entertainment

7.7

Overall

8.1

Crew

8.7

Comfort

8.1

Boarding

8.2

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 37 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 £128, 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 Frontier and Spirit Airlines - these airlines can fly you to your destination from £132 and £133, respectively. These flights start at 35% 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 £65. 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 Air France (100%), Spirit Airlines (100%) or Cathay Pacific (96%) 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 £64. On average you can expect to pay £285. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £128.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

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

Fly with Cheapflights

Find the best flight deals on Cheapflights, where travellers can enjoy low prices and a wide availability of flights to their desired destinations.

How does Cheapflights help users find flights from Boston to Chicago?

900+ travel sites are searched through when a user searches for a flight using Cheapflights. From the search interface, users can use filters to choose airlines, airports, flight times, cabin classes and more to their preference. Book your flight to Chicago from Boston today with Cheapflights!

Why should you use Cheapflights to find cheap flight tickets from Boston to Chicago?

Cheapflights helps you find that perfect flight to Chicago from Boston by searching from hundreds of airlines and agencies you know and love. We are also free to use, in case you were wondering!

Can Cheapflights find flights from Boston to Chicago with no change fees?

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.

100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.