Cheap flights from Boston to Chicago from £61

Cheap flights from Boston to Chicago from £61

Trusted by millions

Kiwi.com Guarantee for stress-free travel

One search, all the best deals

Explore flight deals to Chicago

Direct
Tue, Jul 21
Boston BOSChicago ORD
£61
Search
Direct
Wed, Jul 22
Boston BOSChicago ORD
£61
Search
Direct
Tue, Jul 21
Boston BOSChicago ORD
£61
Search
Direct
Tue, Jul 21
Boston BOSChicago ORD
£61
Search
Direct
Wed, Jul 22
Boston BOSChicago ORD
£61
Search
Direct
Tue, Jul 21
Boston BOSChicago ORD
£61
Search

Not happy with the results? Try some of our useful filters

Search by stops

Search by carrier

Search by price

Search by departure date

Direct
Wed, Jul 22 – Sat, Jul 25
Boston BOSChicago ORD
£123
Search
Direct
Tue, Jul 21 – Sat, Jul 25
Boston BOSChicago ORD
£123
Search
Direct
Tue, Jul 21 – Fri, Jul 24
Boston BOSChicago ORD
£123
Search
Direct
Thu, Jul 23 – Sun, Jul 26
Boston BOSChicago ORD
£123
Search
Direct
Thu, Jul 23 – Sat, Jul 25
Boston BOSChicago ORD
£123
Search
Direct
Sat, Jul 18 – Wed, Jul 22
Boston BOSChicago ORD
£134
Search

Not happy with the results? Try some of our useful filters

Search by stops

Search by carrier

Search by price

Search by departure date

How much do flights to Chicago cost?

Cheapest one-way trip

£61

Cheapest nonstop round-trip

£118

Cheapest round-trip

£123

Average round-trip

£158

Nonstop flights in July

£61 – £203

Getting from Chicago's airport to the city center

Fastest options: CTA Blue Line train from O'Hare. Best value: CTA Orange Line from Midway or shared ride services.

Chicago is served by two major airports, each offering a variety of airport transfers to city center destinations. O'Hare International Airport (ORD) lies 27 km northwest of downtown Chicago, while Chicago Midway International Airport (MDW) is located 16 km southwest of the city center. Transport options include the CTA rapid transit trains, buses, taxis, ride-hailing services, and private transfers. Journey times and costs vary depending on the airport, time of day, and traffic conditions.

How to get from O'Hare International Airport (ORD) to Chicago?

Transport Option

Typical Time

Typical Cost

Frequency

Best For

40-50 min

$5; standard fare

every 5–10 min (traffic dependent)

budget travelers to Loop

60-90 min

$2 – $5; combined bus and Metra fare

every 20–30 min (traffic dependent)

northwest suburbs connection

35-70 min

$45 – $65; metered; varies by traffic

on-demand 24/7 (traffic dependent)

door-to-door with luggage

35-70 min

$35 – $75; surge pricing may apply

on-demand 24/7 (traffic dependent)

app-based convenience

35-70 min

$60 – $120; pre-booked; fixed rate

by reservation (traffic dependent)

groups or business travel

How to get from Chicago Midway International Airport (MDW) to Chicago?

Transport Option

Typical Time

Typical Cost

Frequency

Best For

25-30 min

$5; standard fare

every 6–12 min (traffic dependent)

quick access to Loop

20-45 min

$30 – $45; metered; varies by traffic

on-demand 24/7 (traffic dependent)

door-to-door convenience

20-45 min

$25 – $50; surge pricing may apply

on-demand 24/7 (traffic dependent)

flexible pickup location

Notes:

  • Prices in USD; table created in 2025 and subject to change.
  • CTA Ventra cards or contactless payment accepted on Blue and Orange Lines.
  • Taxis are metered; ride-hailing prices vary with demand. Road traffic can significantly affect journey times.
  • We recommend checking official transport websites for your travel planning.

Updated: December 2025

Key info about flying to Chicago

Depart from
Logan International
Arrive to
O Hare International
Average flights per week
373
Flight distance
1392 km
Worth visiting
Art Institute of Chicago

Weekly direct flights

Discover the top airlines offering direct flights from Boston to Chicago in the next month. You’ll find the number of daily direct flights per airline in the chart.

AirlineMon 06.07Tue 07.07Wed 08.07Thu 09.07Fri 10.07Sat 11.07Sun 12.07
United Airlines
19910973
JetBlue Airways
---11---111
Weekly flights: 53 totalDaily flights: 7.57 averageMost flights: Thursday 10 flights
AirlineMon 13.07Tue 14.07Wed 15.07Thu 16.07Fri 17.07Sat 18.07Sun 19.07
United Airlines
91084553
JetBlue Airways
2211---11
Weekly flights: 52 totalDaily flights: 7.43 averageMost flights: Tuesday 10 flights
AirlineMon 20.07Tue 21.07Wed 22.07Thu 23.07Fri 24.07Sat 25.07Sun 26.07
United Airlines
910991093
JetBlue Airways
2222212
Weekly flights: 72 totalDaily flights: 10.29 averageMost flights: Tuesday 10 flights
AirlineMon 27.07Tue 28.07Wed 29.07Thu 30.07Fri 31.07Sat 01.08Sun 02.08
United Airlines
10101091093
JetBlue Airways
2222111
Weekly flights: 72 totalDaily flights: 10.29 averageMost flights: Monday 10 flights

Check-in for a flight from Boston to Chicago

NameCarrier codeIATA CodePassport needed during booking
JetBlue AirwaysJBUB6No
Frontier AirlinesFFTF9No
United AirlinesUALUANo
Allegiant AirAAYG4No
WestJetWJAWSNo

Online check-in is not available for these airlines.

Weather in Chicago

Average Weather

MonthAverage monthly max temperatureAverage monthly min temperature
January-1°C-6°C
February0°C-5°C
March6°C0°C
April11°C5°C
May17°C10°C
June22°C16°C
July26°C20°C
August25°C19°C
September22°C16°C
October15°C10°C
November8°C3°C
December2°C-1°C
Hottest Month
26°C
July
Coldest month
-6°C
January
Sunny days
257
days per year
Snow days
17
days per year

14 day forecast

Saturday
11 Jul
28°C23°C
18 Jul
75%
31°C20°C
Sunday
12 Jul
27°C22°C
19 Jul
81%
26°C22°C
Monday
13 Jul
29°C21°C
20 Jul
17%
24°C20°C
Tuesday
14 Jul
31°C23°C
21 Jul
24°C20°C
Wednesday
15 Jul
32°C24°C
22 Jul
26°C20°C
Thursday
16 Jul
29°C24°C
23 Jul
77%
28°C20°C
Friday
17 Jul
57%
25°C21°C
24 Jul
23°C21°C
Book your trip to arrive at O Hare International, Chicago Midway International, or Chicago Rockford International. The distance between Boston and Chicago is 1392 km. The most popular airlines for this route are JetBlue Airways, Frontier Airlines, United Airlines, Allegiant Air, and WestJet. Boston and Chicago have 373 direct flights per week.

Frequently asked questions

How long does it take to travel from Boston to Chicago?
A one-way nonstop (direct) flight between Boston and Chicago takes around 2.9 hours.
What is the flight distance between Boston and Chicago?
The flight distance between Boston and Chicago is 1392 km.
What airlines offer nonstop (direct) flights between Boston and Chicago?
Several carriers operate flights between Boston and Chicago. Airlines offering nonstop (direct) flights include JetBlue Airways, United Airlines.
What are the most popular routes to and from Boston?
Travelers frequently search for route combinations, such as Boston and London, Barcelona, Orlando, Edinburgh, Mexico City, Miami, Toronto, Atlanta, Tel Aviv, San Juan, San Francisco, Tampa, Lisbon, Washington, D.C., Istanbul, New York, Bogotá, Dallas, San José, Seattle.
What are the most popular routes to and from Chicago?
Travelers frequently search for route combinations, such as Chicago and London, Mexico City, New York, Guadalajara, Edinburgh, Dallas, Manchester, Morelia, Atlanta, Los Angeles, Houston, León, Leeds, Orlando, San Francisco, Philadelphia, Tampa, Miami, Monterrey, Birmingham.
What airports are near Boston?
The main airport in Boston is Logan International. It is also served by Logan International, Bradley International, Rhode Island T. F. Green Int'l Airport, Albany International, Portland International Jetport, Tweed New Haven, Manchester–Boston Regional, Portsmouth International Airport at Pease, Augusta State, Lebanon Municipal.
What airports are near Chicago?
The main airport in Chicago is O Hare International. It is also served by Gerald R. Ford International, Dane County Regional, South Bend International, General Mitchell International, Fort Wayne International, General Wayne A. Downing Peoria International, Quad City International, Central Illinois Regional, Kalamazoo/Battle Creek International, Muskegon County.
Which airlines fly between Boston and Chicago?
Currently, you can fly between Boston and Chicago with JetBlue Airways, Frontier Airlines, United Airlines, Allegiant Air, WestJet.
When’s the best time to travel between Boston and Chicago?
If you don’t have specific dates for your trip between Boston and Chicago, you can enter a date range into the departure and return fields. Most carriers on the Kiwi.com website allow you to search and book up to six months from the day of your search. Order the search results by the best, cheapest, or fastest route, or find the cheapest outbound and return combination in the pricing table.
What flights operate between Boston and Chicago?
How many airports are there near Boston?
How many airports are there near Chicago?
What time do nonstop (direct) flights between Boston and Chicago depart?
What time do nonstop (direct) flights between Boston and Chicago arrive?
What time do flights between Boston and Chicago depart?
What time do flights between Boston and Chicago arrive?

Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any origin and destination in the world by plane. Find the cheapest routes and best deals, as well as the best dates to travel.

Search flightsSearch direct flights

Explore alternative trips

Flights from Boston

Flights to Chicago

Popular routes

The nearest countries with flights to Chicago

Here is a list of countries people are flying from

Other destination countries from Boston

Here is a list of countries people are flying to

Airports near Boston

Airports near Chicago

Download our app

Start your next adventure now. Download our app and explore cheap flights effortlessly!

Search flights
Find the best connection from Boston to Chicago

Search, compare, and book flights to get there.

Search flights