Flights from Boston to Chicago from $31
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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 $31. 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.
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Cheap flights from BostonCheap 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 $31 – the departure date for this flight is 16 January 2025.
14.02.2025
Friday
from $155
OneTwoTrip
Economy
Found 2025-01-08
1 Stopover
6 hours 14 min
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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 $63, the flight dates are: there on 17 January 2025 year and back on 17 January 2025 year.
Frontier Airlines F9 3511
Morning flight
Departure
03.05.25
10:00, Sa
1 Stopover
Trip 2 days
Return
05.05.25
21:21, Mo
Frontier Airlines F9 3347
Morning flight
Departure
02.05.25
10:00, Fr
1 Stopover
Trip 2 days
Return
04.05.25
14:01, Su
United Airlines UA 1833
Day flight
Departure
13.02.25
11:00, Th
1 Stopover
Trip 3 days
Return
16.02.25
02:44, Su
JetBlue Airways B6 311
Day flight
Departure
05.04.25
13:40, Sa
Direct
Trip 1 day
Return
07.04.25
01:05, Mo
Frontier Airlines F9 1215
Evening flight
Departure
09.02.25
17:56, Su
1 Stopover
Trip 13 days
Return
22.02.25
12:25, Sa
United Airlines UA 2040
Evening flight
Departure
05.07.25
21:05, Sa
Direct
Trip 1 day
Return
06.07.25
12:10, Su
American Airlines AA 4725
Day flight
Departure
14.02.25
12:00, Fr
1 Stopover
Trip 2 days
Return
16.02.25
18:43, Su
Southwest Airlines WN 787
Day flight
Departure
17.01.25
12:00, Fr
Direct
Trip 2 days
Return
19.01.25
13:00, Su
United Airlines UA 1414
Day flight
Departure
27.11.25
11:00, Th
Direct
Trip 3 days
Return
30.11.25
13:10, Su
From Boston to Chicago from $59! Airfare Deals by Spirit Airlines
from $59
left 14 days
Sales dates 01 January 2025
Flight dates: 28 January 2025
Boston - Chicago
One way, Economy - from $59
Find flights
From Boston to Chicago from $73! Airfare Deals by JetBlue Airways
from $73
left 5 days
Sales dates 01 January 2025
Flight dates: 18 January 2025
Boston - Chicago
One way, Economy - from $73
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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 10 flights every day, from 2hours 45min. Local departure and arrival times are indicated.
*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.
Average flight time
02:20 min
Distance
847 mi
The earliest flight
00:00
The latest flight
23:55
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.
- United Airlines: UA 203, UA 2214, UA 375
- American Airlines: AA 1427, AA 2178, AA 2265
- Southwest Airlines: WN 1381, WN 4496, WN 2556
- JetBlue Airways: B6 111, B6 311, B6 1711
- Delta Air Lines: DL 5904, DL 5984, DL 6075
- Spirit Airlines: NK 773
*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
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 $38 16 January 2025
from $38 16 January 2025
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 $53 17 January 2025
from $53 17 January 2025
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 $51 21 January 2025
from $51 21 January 2025
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 $31 16 January 2025
from $31 16 January 2025
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 $205 16 January 2025
from $205 16 January 2025
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 $26 21 January 2025
from $26 21 January 2025
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 $38 21 January 2025
from $38 21 January 2025
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 $28 16 January 2025
from $28 16 January 2025
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 $65 15 January 2025
from $65 15 January 2025
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 $31 16 January 2025
from $31 16 January 2025
Tips for buying a ticket
Boston – Chicago – Boston round-trip route are always cheaper than tickets purchased there and back separately.
To start searching for tickets, Specify dates.