Flights from Boston to Chicago: Best prices, time to go and all you need to know

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Route details

1366 km

Distance

Direct flights to Chicago

Weather now

☀️

+25°F

Clear sky

Airports

DPA

52km

ORD

25km

PWK

35km

Select dates to see flight prices to Chicago

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

December

2025

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.

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.

Direct flights from Boston to Chicago

There are 4 airlines that fly directly from Boston to Chicago: JetBlue Airways, American Airlines, Delta Air Lines, United Airlines if you are departing from Boston. Most airlines that have direct connections are departing from General Edward Lawrence Logan International Airport. Most airlines arrive to Chicago O'Hare International Airport. Most flights depart on Tuesday.

Airlines that have direct flights from Boston to Chicago

JetBlue Airways

BOS

ORD

SÁ

American Airlines

BOS

ORD

SÁ

Delta Air Lines

BOS

ORD

SÁ

United Airlines

BOS

ORD

SÁ

The above ratings are provided by Trustpilot.

Airlines that have connecting flights from Boston to Chicago

There are 10 other airlines that fly from Boston to Chicago, including Hawaiian Airlines, Spirit Airlines, Allegiant Air, Frontier Airlines and others.

Hawaiian Airlines

Spirit Airlines

Allegiant Air

Frontier Airlines

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.

4 airlines with direct flights

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. Most airlines like JetBlue Airways, American Airlines, Delta Air Lines, United Airlines with direct flights are flying to Chicago O'Hare International Airport (ORD).

Things to do in Chicago

Some of the activities you can do while travelling to Chicago:

1676 reviews

Big Bus Chicago Hop-On Hop-Off Sightseeing Tour

Bus Tours • Audio Guides • Hop on Hop Off • City Tours

12289 reviews

Chicago Architecture River Cruise

Day Cruises • Architecture Tours • City Tours • Water Tours • Sightseeing Cruises

716 reviews

360 CHICAGO Observation Deck Admission

Attractions & Museums • Observation Decks • Skyscrapers & Towers

1320 reviews

Skydeck Chicago Admission Ticket

Attractions & Museums • Observation Decks • Skyscrapers & Towers

2295 reviews

Chicago Crime and Mob Bus Tour

Bus Tours • Historical Tours • Crime Tours • Viator Plus • Excellent Quality

5519 reviews

Chicago: Gangsters and Ghosts Walking Tour

Historical Tours • Walking Tours • Night Tours • Ghost & Vampire Tours • City Tours

5058 reviews

Chicago River 90-Minute History and Architecture Tour

Day Cruises • City Tours • Water Tours • Likely to Sell Out • Sightseeing Cruises

See all Activities in Chicago

Planning a trip from Boston to Chicago? Check the weather

15 Days Weather Forecast

Here’s how the weather in Chicago looks currently:

Thu, 11 December

☀️

+25°F

Clear sky

5 m/s

59 %

Fri, 12 December

☁️

+30°F

Broken clouds

6 m/s

72 %

Sat, 13 December

☁️

+10°F

Broken clouds

7 m/s

51 %

Sun, 14 December

☁️

+12°F

Scattered clouds

6 m/s

60 %

Mon, 15 December

☁️

+21°F

Broken clouds

7 m/s

45 %

Tue, 16 December

⛅️

+32°F

Few clouds

6 m/s

65 %

Wed, 17 December

☁️

+37°F

Broken clouds

7 m/s

88 %

Thu, 18 December

🌦

+48°F

Rain

9 m/s

87 %

Fri, 19 December

❄️

+30°F

Snow

8 m/s

38 %

Sat, 20 December

🌦

+39°F

Rain

5 m/s

80 %

Sun, 21 December

🌦

+45°F

Rain

2 m/s

100 %

Mon, 22 December

🌦

+61°F

Rain

9 m/s

86 %

Tue, 23 December

☁️

+34°F

Broken clouds

10 m/s

55 %

Wed, 24 December

☁️

+36°F

Broken clouds

4 m/s

61 %

Thu, 25 December

☁️

+36°F

Broken clouds

6 m/s

53 %

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.

✈️

How far is it to fly between Boston and Chicago?

A passenger flying direct from Boston to Chicago will travel around 1366 km.

⏰

How long does it take to travel from Boston to Chicago?

You should expect a flight time of around ∞h NaNm – -∞h NaNm.

🌤️

What’s the weather like in Chicago?

On average you could expect +25°F in January to +75°F in July. Currently, it is Clear sky and +25°F in Chicago.

🛬

Is there a direct connection between Boston and Chicago?

Yes, there are direct flights from Boston to Chicago. You can fly to Chicago 1 day a week: Tuesday.

🛬

Which airlines offer direct flights from Boston to Chicago?

Here are the airlines that have direct connections from Boston to Chicago: JetBlue Airways, American Airlines, Delta Air Lines, United Airlines.

Chicago guide

Chicago themes

This is what Chicago is known for:

Nightlife

Urbanism

Architecture

Food

Family

Location

Chicago is located in USA, 1366 km away from Boston:

Chicago time zone

Chicago jest o 1 godzinę za Boston, gdzie teraz jest 05:33

🕒

05:33 (EST -5)

Time in Chicago right now

Currency and exchange rate

Both Boston and Chicago have the same currency: United States Dollar.

🤑

Exchange rate

Visa to USA

No visa is required for US citizens. Allowed stay is - days¹.

✅

Visa-free

For US citizens

Language in USA

Official language in USA is English. People knowledge of English is native/fluent².

English

Official language

💬

Knowledge of English

Safety

Some areas of Chicago might be sketchy³. Consider a moderate level of caution.

😳

🫤

🤔

😃

😇

Be careful

Air Quality

Chicago generally has a low level of air pollution⁴.

Air pollution: low

Chicago pros and cons

About Avionero

Avionero is a Swedish travel planning startup located in Malmo, founded by Lars Kristensson and Anton Tyulenev.

Using our smart AI Search engine, we combine millions of flight, hotel, and activity options for your trip to Chicago.

4 things to know about Avionero:

We provide the most flexible search

We have the largest inventory of flights

We are not the sellers, but aggregators of flights, hotels & activities

We do not track you to raise prices

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