Flights from Boston to Chicago from $34

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Flights Chicago → Boston
Flights Schedule   Cheap Tickets   Airlines   Airports

Airfare Deals Boston to Chicago

On HolidayPrice.com you will find 6 direct and 4 connecting flights from Boston to Chicago at a price of from $34. You can compare airfare deals from airlines and multiple travel sites, book and save on cheap plane tickets and last minute offers. Also check out BOS - CHI flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from Boston to Chicago (United States) and back without transfers can be found with the help of the calendar. Specify the search parameters: one way or round-trip, payment currency, click on the month/day you need and we will search for flights to Chicago.

You might be interested in this:

Cheap flights from Boston
Cheap flights to Chicago
Airline tickets to United States

One way flight from Boston to Chicago

Below are the prices of tickets for direct one-way flights from Boston to Chicago. The cheapest flight from Boston to Chicago starts from $34 – the departure date for this flight is 06 October 2024.

Sort by: Departure dateCheap flightsFast flightsDirect flights
16.11.2024 Saturday
from $71 City.Travel
Economy Found 2024-10-02
Nonstop 2 hours 56 min
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16.11.2024 Saturday
from $90 MEGO.travel
Economy Found 2024-10-02
1 Stopover 11 hours 50 min
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16.11.2024 Saturday
from $183 MEGO.travel
Economy Found 2024-10-02
2 Stopovers 18 hours 46 min
Find Flights
*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Boston to Chicago

You can buy a round-trip ticket from Boston to Chicago (United States) and back using the table below. The best offer starts from $69, the flight dates are: there on 24 October 2024 year and back on 24 October 2024 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Spirit Airlines NK 174 Day flight
Departure 24.10.24 15:35, Th
Direct Trip 1 day
Return 26.10.24 01:20, Sa
Find Flights from $144
Spirit Airlines NK 174 Day flight
Departure 01.11.24 15:35, Fr
1 Stopover Trip 2 days
Return 03.11.24 10:10, Su
Find Flights from $149
Frontier Airlines F9 1977 Day flight
Departure 28.11.24 11:00, Th
1 Stopover Trip 3 days
Return 01.12.24 05:59, Su
Find Flights from $245
United Airlines UA 2136 Night flight
Departure 28.11.24 00:38, Th
2 Stopovers Trip 3 days
Return 01.12.24 05:59, Su
Find Flights from $339
*Prices include: baggage, hand luggage, airline fees and charges.
From Boston to Chicago from $65! Airfare Deals by Spirit Airlines
from $65 left 114 days
Sales dates 01 October 2024 Flight dates: 28 January 2025
Boston - Chicago One way, Economy - from $65
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Flight Schedule Boston to Chicago 2024

The current flight schedule for the route from Boston to Chicago for today, tomorrow and the next few days. This schedule will help you decide on the time of departure and arrival, the airline, the flight number and the day of the week.

More than 22 flights every day, from 2hours 30min. Local departure and arrival times are indicated.
05:33 → 07:26
American Airlines AA1509 American Airlines AA1509
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
06:00 → 07:48
United Airlines UA1414 United Airlines UA1414
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
06:20 → 08:00
Southwest Airlines WN4218 Southwest Airlines WN4218
BOS → MDW
- - - - - Sa -
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06:50 → 08:25
Southwest Airlines WN4218 Southwest Airlines WN4218
BOS → MDW
Mo - - Th Fr - -
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07:00 → 08:54
American Airlines AA2223 American Airlines AA2223
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
07:20 → 09:10
Delta Air Lines DL2570 Delta Air Lines DL2570
BOS → ORD
Mo Tu We Th Fr - Su
Check price
07:20 → 08:55
Southwest Airlines WN4218 Southwest Airlines WN4218
BOS → MDW
- Tu We - - - -
Check price
07:25 → 09:00
Southwest Airlines WN4218 Southwest Airlines WN4218
BOS → MDW
- - - - - - Su
Check price
08:00 → 09:49
United Airlines UA660 United Airlines UA660
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
08:00 → 09:49
Delta Air Lines DL2570 Delta Air Lines DL2570
BOS → ORD
- - - - - Sa -
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08:15 → 10:08
JetBlue Airways B6311 JetBlue Airways B6311
BOS → ORD
Mo Tu We Th Fr Sa Su
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08:45 → 10:38
American Airlines AA124 American Airlines AA124
BOS → ORD
Mo Tu We Th Fr Sa Su
Check price
Show all

*Schedule is indicated only for direct scheduled flights and low-cost airlines.

Flight Information

Flying to Chicago from Boston takes 02:20 minutes (excluding transfers). The distance between Boston and Chicago is 847 miles (1364 kilometers). Planes depart from Boston between 00:00 and 23:55. The fastest flight from the company United Airlines with flight number UA 789. Flies for just 02:16 minutes with departure from Boston RT128 Railway and arrival in O'Hare.

time

Average flight time

02:20 min

distance

Distance

847 mi

The earliest flight

The earliest flight

00:00

The latest flight

The latest flight

23:55

Airplane

The fastest flight

02:16

Airlines

Direct flight

There are 6 airlines that fly directly from Boston to Chicago. The most popular company carrying out non-stop flights is United Airlines.

*Flight number

Flights with Transfers

Flights with transfers from Boston to Chicago can be bought from 4 airlines:

  • Southwest Airlines: Baltimore
  • JetBlue Airways: Cleveland, Baltimore, Pittsburgh
  • Delta Air Lines: New York
  • Air Canada: Hamilton

*Transit cities

Airports

Airports serving the air communication between Boston and Chicago. You can fly to Chicago from 1 Boston airports. Planes arrive at 2 airport in Chicago.

Boston airports:

Boston RT128 Railway  ~ 4 km*

Chicago airports:

O'Hare  ~ 25 km* from $ 63Chicago Midway  ~ 14 km* from $ 71

*Distance from the airport to the city center

Aircraft

You can fly from Boston to Chicago on board of 6 airlines that utilize 13 aircraft models.

  • Airbus A319
  • Airbus A320
  • Airbus A321
  • Boeing 737
  • Boeing 737-700
  • Boeing 737-800
  • Boeing 737-900
  • Boeing 757-200
  • Boeing 757-300
  • Embraer 170
  • Embraer 175
  • Embraer 190
  • Embraer EMB 175

Connecting cities

The list of cities on transfer flights to Chicago from Boston. The best options are to fly through: Baltimore, Cleveland, New York, Hamilton, Pittsburgh, Detroit.

Baltimore
Cleveland
New York
Hamilton
Pittsburgh
Detroit

Cheap airline tickets from Boston to United States

Here is a list of flights from Boston to United States purchased on HolidayPrice.com in the past 48 hours. If you find an interesting offer for cheap tickets, do not delay your purchase, prices change every 15 minutes.

Boston - New York B6 917 JetBlue Airways Embraer 190
12:10 Boston RT128 Railway
in a way 0 hours 50 min Direct
13:00 John F. Kennedy
Flights
from $42 12 October 2024
Boston - Los Angeles UA 2145 United Airlines Boeing 757-200
16:45 Boston RT128 Railway
in a way 6 hours 0 min Direct
22:45 Los Angeles
Flights
from $58 08 October 2024
Boston - Miami B6 221 JetBlue Airways Airbus A320
03:50 Boston RT128 Railway
in a way 3 hours 8 min Direct
06:58 Palm Beach
Flights
from $56 06 October 2024
Boston - Chicago UA 789 United Airlines Boeing 737-900
02:44 Boston RT128 Railway
in a way 2 hours 16 min Direct
05:00 O'Hare
Flights
from $34 06 October 2024
Boston - San Francisco B6 133 JetBlue Airways Airbus A318/319/320/321
13:52 Boston RT128 Railway
in a way 6 hours 8 min Direct
20:00 San Francisco
Flights
from $224 12 October 2024

All flights from Boston

Flights from United States to Chicago

Here are the cheapest flight bookings from United States to Chicago made by users of our website. If you didn’t find your flight destination, use the search bar at the top of the page.

New York - Chicago UA 761 United Airlines Boeing 737-800
13:00 LaGuardia
in a way 2 hours 0 min Direct
15:00 O'Hare
Flights
from $29 06 October 2024
Los Angeles - Chicago UA 910 United Airlines Boeing 737-800
10:23 Los Angeles
in a way 3 hours 37 min Direct
14:00 O'Hare
Flights
from $41 06 October 2024
Miami - Chicago AA 2796 American Airlines Boeing 767-300
17:05 Miami
in a way 2 hours 55 min Direct
20:00 O'Hare
Flights
from $31 12 October 2024
San Francisco - Chicago UA 1800 United Airlines Airbus A319
04:15 San Francisco
in a way 3 hours 45 min Direct
08:00 O'Hare
Flights
from $70 08 October 2024
Boston - Chicago UA 789 United Airlines Boeing 737-900
02:44 Boston RT128 Railway
in a way 2 hours 16 min Direct
05:00 O'Hare
Flights
from $34 06 October 2024

All flights to Chicago

Tips for buying a ticket

Boston – Chicago – Boston round-trip route are always cheaper than tickets purchased there and back separately.

Cheap flights from Boston to Chicago
Chicago city

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