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Cheap flights from Boston to Chicago from £62

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 14/12. Fares are subject to change and may not be available on all flights or dates of travel.
BOS — CHI
20 Nov — 27 Nov1
1 adult

The best prices from Boston Logan Intl to Chicago are usually found in September or January, booked 23 days in advance, depart on a Wednesday or Tuesday and return on a Wednesday

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 943,810 searches. Data last updated 15 November 2024.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/12

07:25-09:28

Nonstop3h 03m

Chicago O'Hare Intl

Wed 11/12

10:30-13:52

Nonstop2h 22m

£122

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Mon 9/12

06:00-08:06

Nonstop3h 06m

Chicago O'Hare Intl

Wed 11/12

08:51-12:13

Nonstop2h 22m

£123

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 18/12

06:00-10:53

1 stop5h 53m

Chicago O'Hare Intl

Wed 25/12

09:20-12:46

Nonstop2h 26m

£144

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Wed 2/4

08:17-12:40

1 stop5h 23m

Chicago O'Hare Intl

Wed 9/4

17:12-22:42

1 stop4h 30m

£210

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Tue 17/12

09:00-14:00

1 stop6h 00m

Chicago O'Hare Intl

Sat 21/12

12:15-19:40

1 stop6h 25m

£224

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Fri 25/4

11:31-18:39

1 stop8h 08m

Chicago O'Hare Intl

Sun 27/4

18:50-10:35

1 stop14h 45m

£233

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Sat 14/12

16:23-18:19

Nonstop2h 56m

£62

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 9/1

11:25-15:28

1 stop5h 03m

£69

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 21/11

15:45-17:46

Nonstop3h 01m

£75

BostonChicago

BOS - ORD

BOSORD

Boston Logan Intl

Thu 6/2

12:30-22:20

2 stops10h 50m

£113

Flights are sorted by cheapest first

Deals found on 15/11

Showing 1-10 of 14 results
1
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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 15 November 2024.

Round-trip from

£122

One-way from

£62

Popular in

April

Cheapest in

September
Delta
  • Delta
  • 9/12-11/12
  • Nonstop
  • 5h 25m total
  • Boston to Chicago
Search Deals
Delta
  • Delta
  • 14/12
  • Nonstop
  • 3h 03m total
  • Boston to Chicago
Search Deals
High demand for flights, 18% potential price rise
Search Deals
Best time to find cheap flights, 25% potential price drop
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 15 November 2024.

Mon 9/1207:25BOS - ORD
Nonstop3h 03mDelta
Wed 11/1210:30ORD - BOS
Nonstop2h 22mDelta
Deal found 14/11£122
Mon 9/1206:00BOS - ORD
Nonstop3h 06mJetBlue
Wed 11/1208:51ORD - BOS
Nonstop2h 22mJetBlue
Deal found 15/11£123
Wed 18/1206:00BOS - ORD
1 stop5h 53mUnited Airlines
Wed 25/1209:20ORD - BOS
Nonstop2h 26mUnited Airlines
Deal found 15/11£144
Fri 22/1116:40BOS - ORD
1 stop19h 16mSpirit Airlines
Mon 25/1116:45ORD - BOS
Nonstop2h 19mSpirit Airlines
Deal found 14/11£196
Tue 17/1209:00BOS - ORD
1 stop6h 00mSouthwest
Sat 21/1212:15ORD - BOS
1 stop6h 25mSouthwest
Deal found 14/11£224
Wed 20/1108:00BOS - ORD
1 stop4h 45mAmerican Airlines
Thu 21/1113:30ORD - BOS
1 stop4h 12mAmerican Airlines
Deal found 14/11£248

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 8 November 2024.

The best time to book flights from Boston to Chicago is 23 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 £598). Flying from Boston to Chicago in July is currently the most expensive (average of £774). 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 15 November 2024.

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 13% 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 15 November 2024.

The most flights from BOS to CHI are scheduled on a Thursday (64 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (12 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 15 November 2024.
Read reviews from past customers who have flown Delta, JetBlue 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
5,044 reviews
Check prices

Crew

8.7

Entertainment

7.7

Boarding

8.3

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Southwest
8.1
Very Good
5,044 reviews
Southwest
8.1
Very Good
5,044 reviews
Check prices

Crew

8.7

Entertainment

7.7

Boarding

8.3

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Alaska Airlines
8.0
Very Good
9,446 reviews
Southwest
8.1
Very Good
5,044 reviews
Check prices

Crew

8.7

Entertainment

7.7

Boarding

8.3

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

Delta
8.0
Very Good
8,786 reviews
Southwest
8.1
Very Good
5,044 reviews
Check prices

Crew

8.7

Entertainment

7.7

Boarding

8.3

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

JetBlue
7.5
Good
3,435 reviews
Southwest
8.1
Very Good
5,044 reviews
Check prices

Crew

8.7

Entertainment

7.7

Boarding

8.3

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

United Airlines
7.4
Good
9,193 reviews
Southwest
8.1
Very Good
5,044 reviews
Check prices

Crew

8.7

Entertainment

7.7

Boarding

8.3

Comfort

8.1

Food

7.2

Overall

8.1

Reviews

1 / 10

Great service throughout our flight. Easy boarding with early bird check in

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 43 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 £122, Delta will fly you from Boston to Chicago and back. In addition to Delta, many other airlines offer competitively priced options for your trip. Search Cheapflights for deals from JetBlue and United Airlines - these airlines can fly you to your destination from £123 and £144, respectively. These flights start at 36% 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 Delta, with whom users have recently found tickets for as low as £62. However, be on the lookout for offers from JetBlue and United Airlines, 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 Republic Airways (100%), Avianca (100%) or Japan Airlines (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 £66. On average you can expect to pay £97. The most popular route, (Boston Logan Intl - Chicago O'Hare Intl), can usually be booked for £123.

  • 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 £598). Flying from Boston to Chicago in July is currently the most expensive (average of £774). 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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How does Cheapflights help users find flights from Boston to Chicago?

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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.

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