Search Flights from Boston to Chicago

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Route details

JetBlue Airways

BOSORD

02 Aug - 05 Aug

Direct, 2h 58m

£240

3 days ago

JetBlue Airways

BOSORD

02 Aug - 05 Aug

Direct, 2h 58m

£240

3 days ago

JetBlue Airways

BOSORD

02 Aug - 05 Aug

Direct, 2h 58m

£240

3 days ago

Select dates to see flight prices to Chicago

Pick your travel dates to get the cheapest live flight prices to Chicago:

August

2026

Flight prices from Boston to Chicago

Typically the return flight from Boston to Chicago costs about that much:

No data yet

Cheap

Average price

Expensive

We don’t have sufficient data yet to display price ranges. Make a search to get live prices instead.

Flight examples

Here are different examples (return flights) for those prices:

JetBlue Airways

In a few days

BOS

ORD

Direct, 2h 58m

£240

3 days ago

1366 km

Distance

2h 58m

Duration

Which is the cheapest month to fly to Chicago?

Here are approximate min and max prices for Boston to Chicago flight (one-way) at the moment:

We don’t have data for this route yet. Try searching different months by clicking on them below and get a feeling of when it’s best to fly for you.

Is Chicago an expensive destination?

We have compared flights from Boston to Chicago with other routes:

Not enough data

Price per kilometer: -- £ / km

Unfortunately we don’t yet have enough data for this route to tell if it’s expensive or not.

Recently found flights

Return

One way

02 Aug (Sun) - 05 Aug (Wed)02 Aug (Sun) + nights

12:07

BOS

2h 58m

Direct

15:05

ORD

15:56

ORD

2h 27m

Direct

18:23

BOS

£240

Found 3 days ago

Direct flights from Boston to Chicago

We could not found any direct flights to Chicago, if you are flying from Boston. Perhaps try selecting a different origin or search for direct flights to the whole country (USA).

Not enought data yet

Airports in Chicago and Boston

Chicago has 5 airports and Boston has 1 airport.

Chicago

Boston

DuPage Airport (DPA)

52 km from Chicago city center.

🚕

Taxi

🚌

Bus

🚆

Train

🚍

Shuttle

🚇

Subway

Chicago O'Hare International Airport (ORD)

http://www.flychicago.com/ohare/home/pages/default.aspx

25 km from Chicago city center.

🚕

Taxi

~25 min.

🚌

Bus

~55 min.

🚆

Train

🚍

Shuttle

~25 min.

🚇

Subway

~45 min.

Chicago Executive Airport (PWK)

35 km from Chicago city center.

🚕

Taxi

🚌

Bus

🚆

Train

🚍

Shuttle

🚇

Subway

Chicago Midway International Airport (MDW)

http://www.flychicago.com/midway/

14 km from Chicago city center.

🚕

Taxi

~15 min.

🚌

Bus

~35 min.

🚆

Train

🚍

Shuttle

🚇

Subway

~20 min.

Chicago Merrill C Meigs (CGX)

3 km from Chicago city center.

🚕

Taxi

🚌

Bus

🚆

Train

🚍

Shuttle

🚇

Subway

Which airport in Chicago is better?

The closest airport to Chicago city center is Chicago Merrill C Meigs (CGX) with 3 km distance. The quickest way to get to city center is to take a bus from Chicago O'Hare International Airport (ORD), trip will take 55 min.

Planning a trip from Boston to Chicago? Check the weather

15 Days Weather Forecast

Here’s how the weather in Chicago looks currently:

Today, 01 August

🌦

+23°C

Rain

8 m/s

94 %

Sun, 02 August

🌦

+23°C

Rain

8 m/s

76 %

Mon, 03 August

☀️

+23°C

Clear sky

5 m/s

58 %

Tue, 04 August

☀️

+26°C

Clear sky

4 m/s

55 %

Wed, 05 August

☁️

+29°C

Scattered clouds

3 m/s

45 %

Thu, 06 August

🌦

+25°C

Rain

5 m/s

77 %

Fri, 07 August

🌦

+29°C

Rain

6 m/s

55 %

Sat, 08 August

🌦

+31°C

Rain

7 m/s

54 %

Sun, 09 August

🌦

+28°C

Rain

4 m/s

52 %

Mon, 10 August

🌦

+24°C

Rain

2 m/s

59 %

Tue, 11 August

☁️

+25°C

Scattered clouds

4 m/s

54 %

Wed, 12 August

🌦

+21°C

Rain

4 m/s

93 %

Thu, 13 August

🌦

+26°C

Rain

2 m/s

68 %

Fri, 14 August

🌦

+30°C

Rain

5 m/s

63 %

Sat, 15 August

🌦

+29°C

Rain

6 m/s

54 %

FAQ

Flying from Boston to Chicago? Here are some useful things to know:

🛬

What airports does Chicago has?

There are 5 of airports in Chicago: DuPage Airport, Chicago O'Hare International Airport, Chicago Executive Airport, Chicago Midway International Airport, Chicago Merrill C Meigs. The closest one is Chicago Merrill C Meigs which is 3 km away.