Airfare Deals from Chicago to Boston

Find cheap flights from Chicago to Boston at Tripsta.co.uk in just 5 minutes. On the site you can compare flight prices on this route, buy airline tickets costing from £23 and see the aircraft schedule.

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The cheapest flight ticket from Chicago to Boston was found 2 days ago. Its one way cost starts from £23, the departure date is 13 October 2021. The minimum price for a round trip flight starts from £55. This flight fare was found 2 days ago, with the following departure dates: Chicago on 27 October 2021 year, and back from Boston on 30 October 2021 year.

Plane tickets from Chicago to Boston, one way

The table shows the prices of direct flight plane tickets to Boston from Chicago. If you find an interesting air travel offer, do not delay your purchase, last minute offers run out very quickly.

Sort by: Departure dateCheap flightsFast flightsDirect flights
13.10.2021 Wednesday
from £23 Mytrip.com
Economy Found 2 days
1 Stopover 11 hours 52 min
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02.10.2021 Saturday
from £34 MyHolidays
Economy Found yesterday
Nonstop 2 hours 28 min
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15.10.2021 Friday
from £37 Trip.com
Economy Found 2021-09-13
1 Stopover 14 hours 14 min
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08.10.2021 Friday
from £45 Gotogate
Economy Found 2021-09-13
1 Stopover 14 hours 14 min
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13.10.2021 Wednesday
from £45 Mytrip.com
Economy Found 2 days
Nonstop 2 hours 29 min
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24.10.2021 Sunday
from £51 Kissandfly
Economy Found 2021-09-13
1 Stopover 25 hours 39 min
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13.10.2021 Wednesday
from £60 Tickets.ua
Economy Found 2 days
2 Stopovers 26 hours 25 min
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15.10.2021 Friday
from £62 Mytrip.com
Economy Found 2021-09-13
Nonstop 2 hours 29 min
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08.10.2021 Friday
from £66 Kiwi.com
Economy Found 2021-09-13
2 Stopovers 18 hours 29 min
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24.10.2021 Sunday
from £68 Kiwi.com
Economy Found 2021-09-13
2 Stopovers 23 hours 5 min
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24.10.2021 Sunday
from £73 Gotogate
Economy Found 2021-09-13
3 Stopovers 23 hours 42 min
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13.10.2021 Wednesday
from £76 Tickets.ua
Economy Found 2 days
3 Stopovers 49 hours 47 min
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15.10.2021 Friday
from £82 Aviakassa
Economy Found 2021-09-13
3 Stopovers 35 hours 16 min
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15.10.2021 Friday
from £83 Kiwi.com
Economy Found 2021-09-13
2 Stopovers 35 hours 4 min
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03.10.2021 Sunday
from £87 MyHolidays
Economy Found yesterday
Nonstop 2 hours 22 min
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Best Flights: Chicago to Boston and back

The cost of a round trip flight on the Chicago - Boston (United States) route. The cheapest ticket was purchased 2 days ago, its price was from £55. It flies to Boston on 27 October 2021 year and returns to Chicago on 30 October 2021 year.

Sort by: Departure dateCheap flightsTrip timeDirect flights
Spirit Airlines NK 923 Day flight
Departure 27.10.21 12:00, We
1 Stopover Trip 3 days
Return 30.10.21 21:20, Sa
Spirit Airlines NK 3030 Day flight
Departure 02.10.21 12:45, Sa
1 Stopover Trip 4 days
Return 06.10.21 10:45, We
Spirit Airlines NK 3030 Day flight
Departure 01.10.21 13:00, Fr
1 Stopover Trip 2 days
Return 03.10.21 16:02, Su
Spirit Airlines NK 3030 Day flight
Departure 20.09.21 13:00, Mo
1 Stopover Trip 8 days
Return 28.09.21 20:53, Tu
JetBlue Airways B6 312 Day flight
Departure 22.09.21 15:19, We
Direct Trip 3 days
Return 25.09.21 20:10, Sa
Spirit Airlines NK 3030 Day flight
Departure 18.09.21 12:45, Sa
1 Stopover Trip 7 days
Return 25.09.21 20:53, Sa
Spirit Airlines NK 425 Night flight
Departure 17.10.21 00:10, Su
1 Stopover Trip 4 days
Return 21.10.21 11:30, Th
Spirit Airlines NK 572 Day flight
Departure 23.09.21 11:40, Th
1 Stopover Trip 7 days
Return 30.09.21 09:15, Th
Spirit Airlines NK 425 Night flight
Departure 16.10.21 00:10, Sa
1 Stopover Trip 3 days
Return 19.10.21 10:00, Tu
Spirit Airlines NK 425 Night flight
Departure 10.10.21 00:10, Su
1 Stopover Trip 2 days
Return 11.10.21 23:30, Mo
Spirit Airlines NK 425 Night flight
Departure 09.10.21 00:10, Sa
1 Stopover Trip 7 days
Return 16.10.21 09:00, Sa
United Airlines UA 5293 Evening flight
Departure 10.12.21 21:40, Fr
Direct Trip 2 days
Return 12.12.21 23:21, Su
American Airlines AA 863 Day flight
Departure 24.09.21 16:40, Fr
1 Stopover Trip 3 days
Return 27.09.21 20:53, Mo
American Airlines AA 335 Day flight
Departure 07.10.21 16:35, Th
1 Stopover Trip 2 days
Return 09.10.21 23:30, Sa
American Airlines AA 1181 Day flight
Departure 16.12.21 12:00, Th
1 Stopover Trip 3 days
Return 19.12.21 11:30, Su
United Airlines UA 1890 Night flight
Departure 20.11.21 03:10, Sa
Direct Trip 14 days
Return 03.12.21 17:00, Fr
American Airlines AA 1411 Day flight
Departure 17.10.21 11:00, Su
1 Stopover Trip 4 days
Return 21.10.21 10:00, Th
United Airlines UA 2101 Night flight
Departure 17.09.21 00:50, Fr
Direct Trip 1 day
Return 17.09.21 22:25, Fr
JetBlue Airways B6 12 Day flight
Departure 17.03.22 11:30, Th
Direct Trip 3 days
Return 20.03.22 15:30, Su
American Airlines AA 1172 Night flight
Departure 26.12.21 00:29, Su
Direct Trip 7 days
Return 02.01.22 11:05, Su
American Airlines AA 2037 Night flight
Departure 29.11.21 02:10, Mo
1 Stopover Trip 3 days
Return 02.12.21 14:00, Th

*Prices include: baggage, hand luggage, airline fees and charges.

Flight Schedule Chicago to Boston 2021

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 14 flights every day, from 2hours 14min. Local departure and arrival times are indicated.
07:4511:06
United Airlines UA3513 United Airlines UA3513
ORD → BOS
Mo Tu We Th Fr Sa Su
Check price
08:0011:37
American Airlines AA4163 American Airlines AA4163
ORD → BOS
Mo Tu We Th Fr - -
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08:1011:25
Southwest Airlines WN9 Southwest Airlines WN9
MDW → BOS
- - - - - Sa -
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08:3511:50
Southwest Airlines WN3723 Southwest Airlines WN3723
MDW → BOS
- - - - - - Su
Check price
08:4512:00
Southwest Airlines WN2822 Southwest Airlines WN2822
MDW → BOS
- Tu We - - - -
Check price
09:3012:56
JetBlue Airways B64307 JetBlue Airways B64307
ORD → BOS
Mo Tu We Th Fr - Su
Check price
09:5013:17
JetBlue Airways B64307 JetBlue Airways B64307
ORD → BOS
- - - - - Sa -
Check price
10:1513:45
American Airlines AA9443 American Airlines AA9443
ORD → BOS
Mo Tu We Th Fr - Su
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10:1513:45
JetBlue Airways B6312 JetBlue Airways B6312
ORD → BOS
Mo Tu We Th Fr - Su
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10:5114:11
United Airlines UA677 United Airlines UA677
ORD → BOS
Mo Tu We Th Fr Sa Su
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11:0014:29
Delta Air Lines DL5721 Delta Air Lines DL5721
ORD → BOS
Mo Tu We Th Fr Sa Su
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12:1515:35
Southwest Airlines WN237 Southwest Airlines WN237
MDW → BOS
- - - - - Sa -
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Show all

*Schedule is indicated only for direct scheduled flights and lowcost airlines.

Flight information

It takes 02:20 minutes to fly from Chicago to Boston excluding transfers. The distance between the cities is 1364 km or 847 miles. The earliest morning plane from Chicago leaves for Boston at 00:00. And the latest evening flight departs at 23:55.

time

Non-stop 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

The fastest Chicago - Boston flight ticket is provided by United Airlines, the flight number is UA 1420. It is in the air for 01:55 mins, departing from O'Hare at 17:05 and arriving at 19:00 in Boston RT128 Railway. This flight is carried out on a modern Airbus A320 airliner.

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.

  • Southwest Airlines: WN 2417, WN 4501, WN 3653
  • JetBlue Airways: B6 412, B6 1012, B6 312
  • Delta Air Lines: DL 5890, DL 5904, DL 6090
  • United Airlines: UA 342, UA 992, UA 3622
  • American Airlines: AA 140, AA 2384, AA 2723
  • Spirit Airlines: NK 708

*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

Airfare from airports. In Chicago, 2 airports serve all air communications with Boston. Airplanes arrive at 1 airport in Boston.

Chicago airports:

Chicago Midway  ~ 14 km* from £71O'Hare  ~ 25 km* from £35

Boston airports:

Boston RT128 Railway  ~ 4 km*

*Distance from the airport to the city center

Airplanes

12 aircraft models from 6 airlines fly on the Chicago - Boston route. The fastest airliner is the Airbus A320, from the company United Airlines.

  • 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 from Chicago to Boston. 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 Tripsta.co.uk 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 £25
06 October 2021
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 £20
09 October 2021
Chicago - Miami WN 1909 Southwest Airlines Boeing 737-700
13:40 Chicago Midway International Airport
in a way 2 hours 55 min Direct
16:35 Fort Lauderdale Executive Airport
Flights
from £15
16 October 2021
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 £29
05 October 2021
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 £23
13 October 2021

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 £14
30 September 2021
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 £37
25 September 2021
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 £33
07 November 2021
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 £23
13 October 2021
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 £55
21 September 2021

All flights to Boston

Frequently asked question

How much does a plane ticket from Chicago to Boston cost?

The cost of the cheapest one-way flight from Chicago to Boston starts from £23. The departure date of that flight is 13 October 2021.

Round trip costs start from £55, with the departure date there being on 27 October 2021 year, and back on 30 October 2021 year.

Which airlines fly on the Chicago - Boston route?

There are 6 airlines flying directly from Chicago to Boston: Southwest Airlines, JetBlue Airways, Delta Air Lines, United Airlines, American Airlines, Spirit Airlines

And 3 airlines fly with transfers: Southwest Airlines, American Airlines, United Airlines

How long does it take to fly from Chicago to Boston?

The flight time from Chicago to Boston averages 02:20 mins.

Which planes fly to Boston from Chicago?

12 aircraft models fly from Chicago to Boston, overcoming 847 miles in an average of 02:20 mins. The fastest aircraft on this route is Airbus A320 from United Airlines, it flies for 01:55 min.

  • 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

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

To start searching for tickets, Specify dates.

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