Airfare Deals Chicago to Boston

On HolidayPrice.com you will find 6 direct and 3 connecting flights from Chicago to Boston at a price of from $130. 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 CHI - BOS flight schedule to find best flight time, convenient departure and arrival airports.

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The cost of airline tickets from Chicago to Boston (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 Boston.

One way flight from Chicago to Boston

Below are the prices of tickets for direct one-way flights from Chicago to Boston. The cheapest flight from Chicago to Boston starts from $130 – the departure date for this flight is 09 August 2022.

Sort by: Departure dateCheap flightsFast flightsDirect flights
20.07.2022 Wednesday
from $79 Trip.com
Economy Found 2022-06-20
1 Stopover 8 hours 55 min
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20.07.2022 Wednesday
from $107 Trip.com
Economy Found 2022-06-20
Nonstop 2 hours 24 min
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02.07.2022 Saturday
from $141 Travomint
Economy Found 2022-06-19
1 Stopover 5 hours 19 min
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31.07.2022 Sunday
from $147 MyHolidays
Economy Found 2022-06-21
Nonstop 2 hours 15 min
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02.07.2022 Saturday
from $153 Travomint
Economy Found 2022-06-19
Nonstop 2 hours 30 min
Find Flights
31.07.2022 Sunday
from $161 MyHolidays
Economy Found 2022-06-21
1 Stopover 8 hours 20 min
Find Flights
20.07.2022 Wednesday
from $175 Expedia
Economy Found 2022-06-20
2 Stopovers 10 hours 28 min
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31.07.2022 Sunday
from $211 Travomint
Economy Found 2022-06-21
2 Stopovers 13 hours 39 min
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02.07.2022 Saturday
from $273 Travomint
Economy Found 2022-06-19
2 Stopovers 13 hours 20 min
Find Flights
02.07.2022 Saturday
from $808 Flightsmojo
Economy Found 2022-06-19
3 Stopovers 35 hours 15 min
Find Flights
*Prices include: baggage, hand luggage, airline fees and charges.

Round trip from Chicago to Boston

You can buy a round-trip ticket from Chicago to Boston (United States) and back using the table below. The best offer starts from $158, the flight dates are: there on 05 July 2022 year and back on 07 July 2022 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
United Airlines UA 2170 Evening flight
Departure 09.07.22 23:00, Sa
1 Stopover Trip 2 days
Return 12.07.22 10:00, Tu
American Airlines AA 1194 Day flight
Departure 28.07.22 15:00, Th
Direct Trip 5 hours
Return 28.07.22 19:30, Th
JetBlue Airways B6 1012 Night flight
Departure 17.09.22 00:45, Sa
Direct Trip 2 days
Return 18.09.22 20:50, Su
American Airlines AA 1287 Day flight
Departure 27.09.22 13:25, Tu
Direct Trip 7 days
Return 04.10.22 09:30, Tu
American Airlines AA 4153 Day flight
Departure 30.08.22 11:15, Tu
Direct Trip 1 day
Return 31.08.22 12:00, We
United Airlines UA 1855 Day flight
Departure 30.06.22 13:53, Th
Direct Trip 7 days
Return 07.07.22 11:31, Th
United Airlines UA 677 Day flight
Departure 29.06.22 15:35, We
Direct Trip 4 days
Return 04.07.22 01:09, Mo
United Airlines UA 2306 Evening flight
Departure 28.06.22 18:55, Tu
Direct Trip 8 days
Return 06.07.22 11:31, We
Southwest Airlines WN 2256 Evening flight
Departure 06.07.22 22:55, We
1 Stopover Trip 13 days
Return 20.07.22 02:40, We
Southwest Airlines WN 2108 Night flight
Departure 06.07.22 00:00, We
1 Stopover Trip 14 days
Return 20.07.22 02:40, We
Southwest Airlines WN 938 Night flight
Departure 13.07.22 01:50, We
Direct Trip 2 days
Return 15.07.22 02:40, Fr
United Airlines UA 1046 Night flight
Departure 28.06.22 02:08, Tu
Direct Trip 9 days
Return 07.07.22 02:40, Th
XX 5708 Day flight
Departure 07.09.22 14:40, We
Direct Trip 21 day
Return 28.09.22 10:45, We
XX 5715 Day flight
Departure 14.09.22 11:15, We
Direct Trip 14 days
Return 28.09.22 10:45, We
XX 5715 Day flight
Departure 13.09.22 11:15, Tu
Direct Trip 15 days
Return 28.09.22 10:45, We
XX 5715 Day flight
Departure 21.09.22 11:15, We
Direct Trip 7 days
Return 28.09.22 10:45, We
Southwest Airlines WN 1552 Night flight
Departure 05.07.22 03:00, Tu
1 Stopover Trip 16 days
Return 21.07.22 02:40, Th
Southwest Airlines WN 1552 Night flight
Departure 04.07.22 03:00, Mo
1 Stopover Trip 16 days
Return 20.07.22 02:40, We
American Airlines AA 1150 Day flight
Departure 10.09.22 15:22, Sa
1 Stopover Trip 4 days
Return 14.09.22 12:00, We
American Airlines AA 4153 Day flight
Departure 08.09.22 11:15, Th
Direct Trip 2 days
Return 10.09.22 10:50, Sa
American Airlines AA 4153 Day flight
Departure 15.09.22 11:15, Th
Direct Trip 12 days
Return 27.09.22 23:11, Tu
American Airlines AA 4153 Day flight
Departure 17.08.22 11:15, We
Direct Trip 24 days
Return 10.09.22 10:50, Sa
United Airlines UA 1270 Day flight
Departure 28.09.22 11:00, We
1 Stopover Trip 7 days
Return 05.10.22 10:00, We
United Airlines UA 1270 Day flight
Departure 20.09.22 11:00, Tu
1 Stopover Trip 14 days
Return 04.10.22 11:30, Tu
Southwest Airlines WN 3009 Evening flight
Departure 26.08.22 20:45, Fr
1 Stopover Trip 4 days
Return 30.08.22 09:20, Tu
American Airlines AA 404 Evening flight
Departure 12.09.22 22:37, Mo
1 Stopover Trip 7 days
Return 19.09.22 12:00, Mo
American Airlines AA 636 Evening flight
Departure 24.09.22 20:14, Sa
1 Stopover Trip 3 days
Return 27.09.22 12:00, Tu
American Airlines AA 1120 Day flight
Departure 17.09.22 11:09, Sa
1 Stopover Trip 2 days
Return 19.09.22 12:00, Mo
American Airlines AA 523 Day flight
Departure 04.09.22 11:10, Su
1 Stopover Trip 4 days
Return 08.09.22 09:30, Th
American Airlines AA 2726 Day flight
Departure 23.08.22 14:58, Tu
1 Stopover Trip 7 hours
Return 23.08.22 21:30, Tu
United Airlines UA 2170 Evening flight
Departure 11.07.22 23:00, Mo
1 Stopover Trip 2 days
Return 13.07.22 13:43, We
American Airlines AA 636 Evening flight
Departure 31.08.22 20:15, We
1 Stopover Trip 6 days
Return 06.09.22 12:00, Tu
American Airlines AA 1984 Evening flight
Departure 03.09.22 17:15, Sa
1 Stopover Trip 7 days
Return 10.09.22 15:01, Sa
American Airlines AA 404 Evening flight
Departure 27.08.22 23:33, Sa
1 Stopover Trip 7 days
Return 03.09.22 15:15, Sa
American Airlines AA 1784 Morning flight
Departure 02.08.22 10:30, Tu
1 Stopover Trip 7 days
Return 09.08.22 10:00, Tu
United Airlines UA 1046 Night flight
Departure 08.07.22 02:08, Fr
Direct Trip 4 days
Return 12.07.22 10:00, Tu
Southwest Airlines WN 3009 Evening flight
Departure 20.07.22 20:45, We
1 Stopover Trip 5 days
Return 26.07.22 02:40, Tu
American Airlines AA 1854 Day flight
Departure 04.08.22 11:31, Th
1 Stopover Trip 7 days
Return 11.08.22 10:00, Th
American Airlines AA 1120 Day flight
Departure 06.09.22 12:34, Tu
1 Stopover Trip 4 days
Return 10.09.22 11:30, Sa
American Airlines AA 946 Morning flight
Departure 16.08.22 10:00, Tu
1 Stopover Trip 7 days
Return 23.08.22 10:00, Tu
American Airlines AA 1652 Day flight
Departure 26.07.22 13:37, Tu
1 Stopover Trip 7 days
Return 02.08.22 12:12, Tu
American Airlines AA 523 Day flight
Departure 13.07.22 11:06, We
1 Stopover Trip 7 days
Return 20.07.22 10:00, We
American Airlines AA 523 Day flight
Departure 19.07.22 11:06, Tu
1 Stopover Trip 7 days
Return 26.07.22 11:00, Tu
American Airlines AA 1854 Day flight
Departure 11.08.22 11:31, Th
1 Stopover Trip 7 days
Return 18.08.22 11:30, Th
American Airlines AA 1854 Day flight
Departure 18.08.22 11:32, Th
1 Stopover Trip 7 days
Return 25.08.22 10:00, Th
American Airlines AA 1120 Day flight
Departure 10.08.22 12:31, We
1 Stopover Trip 20 days
Return 30.08.22 16:56, Tu
American Airlines AA 1002 Day flight
Departure 24.08.22 13:50, We
1 Stopover Trip 6 days
Return 30.08.22 16:30, Tu
United Airlines UA 1270 Day flight
Departure 22.09.22 11:00, Th
1 Stopover Trip 17 days
Return 08.10.22 23:06, Sa
Southwest Airlines WN 3009 Evening flight
Departure 22.07.22 20:45, Fr
1 Stopover Trip 3 days
Return 26.07.22 02:40, Tu
American Airlines AA 2682 Night flight
Departure 25.06.22 01:35, Sa
Direct Trip 18 days
Return 13.07.22 02:40, We
United Airlines UA 254 Day flight
Departure 26.06.22 11:00, Su
Direct Trip 9 days
Return 05.07.22 10:00, Tu
American Airlines AA 1792 Day flight
Departure 01.10.22 11:15, Sa
Direct Trip 4 days
Return 05.10.22 12:00, We
American Airlines AA 1792 Day flight
Departure 26.09.22 11:15, Mo
Direct Trip 2 days
Return 28.09.22 12:00, We
American Airlines AA 1792 Day flight
Departure 19.09.22 11:15, Mo
Direct Trip 16 days
Return 05.10.22 12:00, We
Southwest Airlines WN 938 Night flight
Departure 16.08.22 01:50, Tu
Direct Trip 6 days
Return 22.08.22 01:04, Mo
United Airlines UA 6007 Evening flight
Departure 08.07.22 21:00, Fr
1 Stopover Trip 2 days
Return 10.07.22 09:30, Su
JetBlue Airways B6 1012 Night flight
Departure 10.09.22 00:45, Sa
Direct Trip 12 days
Return 21.09.22 20:50, We
United Airlines UA 254 Day flight
Departure 02.07.22 11:00, Sa
Direct Trip 2 days
Return 04.07.22 09:20, Mo
United Airlines UA 677 Day flight
Departure 23.07.22 15:36, Sa
Direct Trip 5 days
Return 29.07.22 02:40, Fr
Southwest Airlines WN 2256 Evening flight
Departure 19.08.22 22:55, Fr
1 Stopover Trip 1 day
Return 21.08.22 10:00, Su
Southwest Airlines WN 2256 Evening flight
Departure 25.08.22 22:55, Th
1 Stopover Trip 4 days
Return 30.08.22 02:55, Tu
United Airlines UA 2302 Night flight
Departure 30.08.22 02:08, Tu
Direct Trip 22 days
Return 21.09.22 11:30, We
United Airlines UA 2302 Night flight
Departure 03.09.22 02:08, Sa
Direct Trip 11 days
Return 14.09.22 11:30, We
United Airlines UA 2302 Night flight
Departure 23.08.22 02:08, Tu
Direct Trip 21 day
Return 13.09.22 10:00, Tu
United Airlines UA 1217 Day flight
Departure 03.08.22 11:00, We
Direct Trip 28 days
Return 31.08.22 11:31, We
United Airlines UA 656 Evening flight
Departure 21.07.22 23:25, Th
Direct Trip 1 day
Return 23.07.22 10:00, Sa
American Airlines AA 1167 Day flight
Departure 01.07.22 16:56, Fr
1 Stopover Trip 4 days
Return 05.07.22 11:00, Tu
United Airlines UA 1503 Night flight
Departure 01.10.22 02:37, Sa
Direct Trip 25 days
Return 26.10.22 10:00, We
American Airlines AA 4153 Day flight
Departure 09.08.22 11:20, Tu
Direct Trip 14 days
Return 23.08.22 09:30, Tu
United Airlines UA 499 Day flight
Departure 20.08.22 12:43, Sa
Direct Trip 1 day
Return 21.08.22 11:31, Su
United Airlines UA 2164 Day flight
Departure 29.09.22 12:15, Th
1 Stopover Trip 5 days
Return 04.10.22 11:30, Tu
United Airlines UA 2170 Evening flight
Departure 10.07.22 23:00, Su
1 Stopover Trip 1 day
Return 12.07.22 10:00, Tu
American Airlines AA 1167 Day flight
Departure 25.06.22 16:56, Sa
1 Stopover Trip 2 days
Return 28.06.22 02:25, Tu
American Airlines AA 1941 Evening flight
Departure 30.07.22 21:26, Sa
1 Stopover Trip 7 days
Return 06.08.22 10:00, Sa
United Airlines UA 2170 Evening flight
Departure 27.07.22 23:00, We
1 Stopover Trip 7 days
Return 03.08.22 11:31, We
United Airlines UA 1046 Night flight
Departure 15.07.22 02:08, Fr
1 Stopover Trip 6 days
Return 21.07.22 13:43, Th
United Airlines UA 2170 Evening flight
Departure 17.07.22 23:00, Su
1 Stopover Trip 4 days
Return 21.07.22 13:43, Th
JetBlue Airways B6 9521 Night flight
Departure 19.09.22 00:45, Mo
Direct Trip 7 days
Return 25.09.22 20:50, Su
XX 5689 Evening flight
Departure 18.07.22 21:30, Mo
Direct Trip 6 days
Return 24.07.22 21:20, Su
American Airlines AA 1181 Day flight
Departure 12.08.22 11:20, Fr
1 Stopover Trip 4 days
Return 16.08.22 10:00, Tu
United Airlines UA 2302 Night flight
Departure 06.08.22 02:08, Sa
Direct Trip 25 days
Return 31.08.22 11:31, We
United Airlines UA 2302 Night flight
Departure 29.08.22 02:08, Mo
Direct Trip 1 day
Return 30.08.22 11:31, Tu
United Airlines UA 2302 Night flight
Departure 09.08.22 02:08, Tu
Direct Trip 21 day
Return 30.08.22 11:31, Tu
United Airlines UA 656 Evening flight
Departure 13.08.22 23:25, Sa
Direct Trip 25 days
Return 07.09.22 11:30, We
XX 5715 Day flight
Departure 11.09.22 11:15, Su
Direct Trip 3 days
Return 14.09.22 10:45, We
United Airlines UA 1046 Night flight
Departure 16.07.22 02:08, Sa
1 Stopover Trip 11 days
Return 27.07.22 13:43, We
United Airlines UA 2170 Evening flight
Departure 16.07.22 23:00, Sa
1 Stopover Trip 3 days
Return 19.07.22 11:31, Tu
Delta Air Lines DL 2614 Evening flight
Departure 21.08.22 22:00, Su
1 Stopover Trip 9 days
Return 30.08.22 10:45, Tu
American Airlines AA 1854 Day flight
Departure 29.07.22 11:31, Fr
1 Stopover Trip 7 days
Return 05.08.22 10:00, Fr
United Airlines UA 1046 Night flight
Departure 26.07.22 02:08, Tu
Direct Trip 28 days
Return 23.08.22 11:31, Tu
American Airlines AA 4153 Day flight
Departure 05.09.22 11:15, Mo
Direct Trip 7 days
Return 12.09.22 21:42, Mo
American Airlines AA 1792 Day flight
Departure 25.09.22 11:15, Su
Direct Trip 10 days
Return 05.10.22 12:00, We
Delta Air Lines DL 2614 Evening flight
Departure 14.08.22 22:00, Su
1 Stopover Trip 27 days
Return 10.09.22 10:45, Sa
Southwest Airlines WN 2887 Evening flight
Departure 01.09.22 17:35, Th
1 Stopover Trip 4 days
Return 05.09.22 09:20, Mo
United Airlines UA 1046 Night flight
Departure 01.08.22 02:08, Mo
Direct Trip 5 days
Return 06.08.22 11:31, Sa
Spirit Airlines NK 3057 Evening flight
Departure 23.09.22 19:51, Fr
1 Stopover Trip 2 days
Return 25.09.22 19:25, Su
United Airlines UA 1217 Day flight
Departure 07.08.22 11:00, Su
Direct Trip 24 days
Return 31.08.22 11:31, We
United Airlines UA 656 Evening flight
Departure 06.08.22 23:25, Sa
Direct Trip 25 days
Return 31.08.22 11:31, We
United Airlines UA 2302 Night flight
Departure 02.08.22 02:08, Tu
Direct Trip 28 days
Return 30.08.22 11:31, Tu
Spirit Airlines NK 426 Day flight
Departure 24.07.22 16:05, Su
1 Stopover Trip 3 days
Return 27.07.22 15:53, We
*Prices include: baggage, hand luggage, airline fees and charges.
Not found promotions and sales.

Flight Schedule Chicago to Boston 2022

The current flight schedule for the route from Chicago to Boston 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 12 flights every day, from 2hours 5min. Local departure and arrival times are indicated.
06:0011:30
Southwest Airlines WN2864 Southwest Airlines WN2864
MDW → BOS
- - - - - Sa -
Check price
06:1309:31
American Airlines AA1024 American Airlines AA1024
ORD → BOS
Mo Tu We Th Fr - Su
Check price
06:3009:53
JetBlue Airways B62112 JetBlue Airways B62112
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
07:1510:30
United Airlines UA2016 United Airlines UA2016
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
08:0011:15
Southwest Airlines WN1014 Southwest Airlines WN1014
MDW → BOS
Mo Tu We Th Fr - Su
Check price
08:5012:07
United Airlines UA573 United Airlines UA573
ORD → BOS
- - - - - Sa -
Check price
10:3513:45
Southwest Airlines WN3254 Southwest Airlines WN3254
MDW → BOS
- - - - - Sa -
Check price
10:5614:20
United Airlines UA677 United Airlines UA677
ORD → BOS
- - - - - - Su
Check price
10:5714:21
United Airlines UA677 United Airlines UA677
ORD → BOS
Mo Tu We Th Fr - -
Check price
11:0214:26
United Airlines UA677 United Airlines UA677
ORD → BOS
- - - - - Sa -
Check price
12:0015:18
American Airlines AA2264 American Airlines AA2264
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
14:0017:20
United Airlines UA2306 United Airlines UA2306
ORD → BOS
Mo - - Th Fr Sa Su
Check price
Show all

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

Flight Information

Flying to Boston from Chicago takes 02:20 minutes (excluding transfers). The distance between Chicago and Boston is 847 miles (1364 kilometers). Planes depart from Chicago between 00:00 and 23:55. The fastest flight from the company United Airlines with flight number UA 1420. Flies for just 01:55 minutes with departure from O'Hare and arrival in Boston RT128 Railway.

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

01:55

Airlines

Direct flight

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

*Flight number

Flights with Transfers

Flights with transfers from Chicago to Boston can be bought from 3 airlines:

  • Southwest Airlines: Detroit, Cleveland, Nashville
  • American Airlines: Detroit, Saint Paul Island, Nashville
  • United Airlines: Detroit, Hamilton, Saint Paul Island

*Transit cities

Airports

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

Chicago airports:

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

Boston airports:

Boston RT128 Railway  ~ 4 km*

*Distance from the airport to the city center

Aircraft

You can fly from Chicago to Boston on board of 6 airlines that utilize 12 aircraft models.

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

Connecting cities

The list of cities on transfer flights to Boston from Chicago. The best options are to fly through: Detroit, Saint Paul Island, Cleveland, Nashville.

Cheap airline tickets from Chicago to United States

Here is a list of flights from Chicago 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.

Chicago - New York AA 2382 American Airlines Boeing 737-800
01:13 O'Hare
in a way 1 hours 47 min Direct
03:00 Newark Liberty
Flights
from $98
01 July 2022
Chicago - Los Angeles AA 2744 American Airlines Airbus A321
20:03 O'Hare
in a way 3 hours 57 min Direct
00:00 Los Angeles
Flights
from $153
24 August 2022
Chicago - Miami WN 1909 Southwest Airlines Boeing 737-700
13:40 Chicago Midway
in a way 2 hours 55 min Direct
16:35 Fort Lauderdale Executive Airport
Flights
from $75
06 July 2022
Chicago - San Francisco AA 1312 American Airlines Boeing 737-800
17:55 O'Hare
in a way 4 hours 5 min Direct
22:00 Norman Y. Mineta San Jose
Flights
from $161
10 September 2022
Chicago - Boston UA 1420 United Airlines Airbus A320
17:05 O'Hare
in a way 1 hours 55 min Direct
19:00 Boston RT128 Railway
Flights
from $130
09 August 2022

All flights from Chicago

Flights from United States to Boston

Here are the cheapest flight bookings from United States to Boston 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 - Boston AA 2121 American Airlines Embraer 190
16:00 LaGuardia
in a way 1 hours 0 min Direct
17:00 Boston RT128 Railway
Flights
from $77
10 October 2022
Los Angeles - Boston B6 504 JetBlue Airways Airbus A320
08:00 Long Beach Airport
in a way 5 hours 14 min Direct
13:14 Boston RT128 Railway
Flights
from $278
11 July 2022
Miami - Boston B6 22 JetBlue Airways Airbus A320
03:12 Palm Beach
in a way 2 hours 56 min Direct
06:08 Boston RT128 Railway
Flights
from $107
30 June 2022
Chicago - Boston UA 1420 United Airlines Airbus A320
17:05 O'Hare
in a way 1 hours 55 min Direct
19:00 Boston RT128 Railway
Flights
from $130
09 August 2022
San Francisco - Boston B6 834 JetBlue Airways Airbus A318/319/320/321
06:35 San Francisco
in a way 5 hours 26 min Direct
12:01 Boston RT128 Railway
Flights
from $329
02 July 2022

All flights to Boston

Tips for buying a ticket

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

Cheap flights from Chicago to Boston
Boston city

To start searching for tickets, Specify dates.

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