Flights Boston — Chicago

Q: Which airlines fly from Boston to Chicago?

United Airlines, American Airlines, JetBlue, Southwest, and several other American and international carriers operate on this route.

Cheap flights Boston — Chicago

Below you can see the best deals on Boston — Chicago flights for the upcoming dates. Compare direct and connecting flights from different airlines and pick the ticket that suits you best.

The lowest price in the next 2 months is on August 11 — from 5 631 ₽.

Top 10 cheap flights Boston — Chicago

Direct flights Boston — Chicago

Offers on non-stop flights from Boston to Chicago for the upcoming dates. A direct flight is faster and more convenient — especially when travelling with luggage or children.

The fastest non-stop flight is operated by United Airlines — about 2 h 44 m in the air.

Top 10 direct flights Boston — Chicago

About the Boston — Chicago flight

On this page, you can find and buy flight tickets from Boston to Chicago. The flight distance is 1,369 km, and a high frequency of around 131 flights per week makes it easy to find a convenient departure time. Be sure to check the information on how to get to the airport before you leave.

Regular service is provided by American Airlines, United Airlines, and JetBlue. Ticket prices depend on the season and how far in advance you book, so we recommend using the price trends chart and studying ways of how to get from the airport after landing.

Return route: Chicago → Boston tickets

Flight schedule Boston — Chicago

The table shows direct flights Boston → Chicago for the selected date. The flight takes about 2h 52m. Regular flights are operated by American Airlines, United Airlines, Southwest Airlines and Delta. Departures from Logan International Airport, arrivals at O'Hare International Airport, Chicago Midway International Airport and Midway International Airport.

Each row shows: local departure time, destination city and airport, flight number with airline, terminal or gate and status. Click a flight to open its details and switch to search. To view another day, change the date above the table.

Today

Any time

Departure time

Flight

Terminal and gate

Status

When to fly

The warmest weather in Chicago occurs in July, when the average high reaches 26.5°C. January is the coldest month with temperatures as low as -5°C, while the peak precipitation and most humid weather are typically recorded in May.

The lowest ticket prices are observed in November, starting from 5,218 ₽. Currently, the most expensive period to fly is February, with prices starting from 8,058 ₽.

September is a great time to visit: the city enjoys comfortable temperatures around 23.5°C with moderate ticket costs. During the winter months, be sure to consider the risk of flight delays due to weather conditions.

Ticket prices · Boston → Chicago

Temperature · Chicago

Dry and wet days · Chicago

Wind speed and direction · Chicago

Flight prices by day Boston — Chicago

Below is the calendar of lowest prices for Boston — Chicago flights by day. Pick a convenient date and see the fare instantly. The cheapest flights on this route start at 5,218 RUB in November, the most expensive reach around 8,058 RUB in February. If your dates are flexible, the calendar helps you pick the lowest fare for the period you need. To view round-trip prices, switch to the “Round-trip” tab above the calendar and pick a departure date — the right-side calendar will then highlight the lowest return fares for each day.

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How to book Boston — Chicago flights smarter

We recommend planning your ticket purchase 4–6 weeks before departure to find deals from 5,218 ₽.
Compare fares from Southwest (WN) and JetBlue (B6), as low-cost carriers often offer more favorable baggage terms on flights to Chicago.
Use the low-price calendar on this page: mid-week departures (Tuesday or Wednesday) are usually cheaper than weekend flights.
Pay attention to the arrival airport, as choosing between O'Hare and Midway can affect the final cost of your transfer to the city center.

Airlines

Major carriers such as United Airlines, American Airlines, and JetBlue operate on the Boston–Chicago route, providing the bulk of the 131 weekly flights. Most flights are non-stop, making this a convenient route for both business and leisure travel. Detailed information on departure times and route options can be found in the list of airlines below.

American AirlinesAA
45/wk
WebsiteFleet: 965211 M pax/yr
- Direct flight BOS → ORD45/wk
  Ave. duration
  3h 6m
  Days
  MoTuWeThFrSaSu
34.0%Open →
United AirlinesUA
41/wk
WebsiteFleet: 956165 M pax/yr
- Direct flight BOS → ORD41/wk
  Ave. duration
  2h 55m
  Days
  MoTuWeThFrSaSu
31.0%Open →
Southwest AirlinesWN
13/wk
WebsiteFleet: 817140 M pax/yr
- Direct flight BOS → MDW13/wk
  Ave. duration
  2h 44m
  Days
  MoTuWeThFrSaSu
9.6%Open →
DeltaDL
12/wk
WebsiteFleet: 986190 M pax/yr
- Direct flight BOS → ORD12/wk
  Ave. duration
  3h
  Days
  MoTuWeThFrSaSu
9.4%Open →
JetBlueB6
9/wk
WebsiteFleet: 30742.5 M pax/yr
- Direct flight BOS → ORD9/wk
  Ave. duration
  3h
  Days
  MoTuWeThFrSaSu
6.6%Open →
Japan AirlinesJL
3/wk
WebsiteFleet: 14540 M pax/yr
- Direct flight BOS → ORD3/wk
2.5%Open →
IberiaIB
3/wk
WebsiteFleet: 9224 M pax/yr
- Direct flight BOS → ORD3/wk
2.3%Open →
British AirwaysBA
3/wk
WebsiteFleet: 29243 M pax/yr
- Direct flight BOS → ORD3/wk
2.0%Open →
Alaska AirlinesAS
2/wk
WebsiteFleet: 31545 M pax/yr
- Direct flight BOS → ORD2/wk
  Ave. duration
  2h 58m
  Days
  MoTuWeThFrSaSu
1.3%Open →
Virgin AtlanticVS
1/wk
WebsiteFleet: 415.3 M pax/yr
- Direct flight BOS → ORD1/wk
0.5%Open →
SASSK
1/wk
WebsiteFleet: 13524 M pax/yr
- Direct flight BOS → ORD1/wk
0.3%Open →
Latam Airlines GroupLA
1/wk
WebsiteFleet: 34782 M pax/yr
- Direct flight BOS → ORD1/wk
  Ave. duration
  2h 52m
  Days
  MoTuWeThFrSaSu
0.3%Open →

Cities and airports on the Boston — Chicago route

Flights Boston — Chicago depart from Logan International Airport and land at O'Hare International Airport, Chicago Midway International Airport, Midway International Airport and Chicago Rockford International Airport. Below are pages for the cities, countries and airports on this route: airlines, schedules and travel guides.

Departure

Boston

BOS

United States

About the city Getting there Weather About United States

Arrival

Chicago

CHI

United States

About the city Getting there Weather About United States

Departure airports

Logan International AirportBOS
About

Arrival airports

O'Hare International AirportORD
About
Chicago Midway International AirportMDW
About
Midway International AirportNOH
About
Chicago Rockford International AirportRFD
About

Articles about Chicago

View all

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FAQ: Boston — Chicago flights

How long is the flight from Boston to Chicago?

The distance between the cities is 1,369 km. A direct flight usually takes about 2 hours and 10 minutes, depending on the airline and weather conditions.

Which airlines fly from Boston to Chicago?

United Airlines, American Airlines, JetBlue, Southwest, and several other American and international carriers operate on this route.

Are there direct flights?

Yes, there are many direct flights between the cities every day, allowing you to choose a convenient departure time in the morning, afternoon, or evening.

How much is the cheapest ticket?

Flight prices constantly change based on demand. You can see the current minimum for specific dates in the low-price calendar on this page.

Which airport does the flight arrive at?

Flights from Boston arrive at the main Chicago airports. Detailed information about the arrival terminal can be found in the details of your selected ticket.

Where else to fly from Boston

New York City∙July 4

RUB 5,990

Washington, D.C.∙July 14

RUB 4,173

Where else to fly to Chicago

New York City∙July 14

RUB 6,660

Washington, D.C.∙July 3