Cheap Flights from Chicago, IL to Boston, MA from $61

Return flight: Boston – Chicago

On Cheapflightsplus.com you will find 14 direct and 23 connecting flights from Chicago to Boston at a price of from $44. You can compare airfare deals from 4 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.

Find One-Way and Round-Trip Chicago to Boston Flight Deals

To find the cheapest one way airline ticket select the date with the lowest price on the calendar below and click «Find Flights». To search for round-trip flight deals click on the link «Check prices for return flights» and select the date of the return flight. Cheapest flights in November: $61 (one-way), $105 (round-trip).
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Full flight schedule will help you in detecting at what time planes fly from Chicago to Boston. You can also specify the concrete flights and airlines on the route and how long the flight actually is. Use the calendar for today, tomorrow or other specific date as some flights are available only on certain days of the week.
Departure Arrival Flight Details Flight Duration Price
07:15 — 10:26
07:15 — 10:26 AA2384 American Airlines
Chicago — Boston
2h 11m
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from$44
07:45 — 10:56
07:45 — 10:56 UA992 United Airlines
Chicago — Boston
2h 11m
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from$63
08:45 — 11:58
08:45 — 11:58 AA2723 American Airlines
Chicago — Boston
2h 13m
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from$53
08:55 — 12:06
08:55 — 12:06 UA1420 United Airlines
Chicago — Boston
2h 11m
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from$65
10:05 — 13:19
10:05 — 13:19 AA2264 American Airlines
Chicago — Boston
2h 14m
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from$53
11:40 — 14:51
11:40 — 14:51 UA532 United Airlines
Chicago — Boston
2h 11m
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from$69
11:58 — 15:10
11:58 — 15:10 B6312 JetBlue
Chicago — Boston
2h 12m
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from$63
13:31 — 16:43
13:31 — 16:43 AA1360 American Airlines
Chicago — Boston
2h 12m
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from$78
14:00 — 17:20
14:00 — 17:20 UA578 United Airlines
Chicago — Boston
2h 20m
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from$77
15:40 — 18:53
15:40 — 18:53 UA913 United Airlines
Chicago — Boston
2h 13m
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from$72
16:55 — 20:07
16:55 — 20:07 AA1251 American Airlines
Chicago — Boston
2h 12m
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from$53
18:03 — 21:16
18:03 — 21:16 UA790 United Airlines
Chicago — Boston
2h 13m
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from$102
18:34 — 21:50
18:34 — 21:50 AA1172 American Airlines
Chicago — Boston
2h 16m
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from$85
20:21 — 23:32
20:21 — 23:32 AA2682 American Airlines
Chicago — Boston
2h 11m
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from$53
05:25 — 12:12
05:25 — 08:22 AA2215 American Airlines
Chicago — Philadelphia
2h 23m stop
10:45 — 12:12 AA689 American Airlines
Philadelphia — Boston
5h 47m
including layover
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from$207
05:25 — 12:35
05:25 — 08:22 AA2215 American Airlines
Chicago — Philadelphia
2h 53m stop
11:15 — 12:35 AA1898 American Airlines
Philadelphia — Boston
6h 10m
including layover
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from$207
05:49 — 13:31
05:49 — 08:43 AA2523 American Airlines
Chicago — Charlotte
2h 41m stop
11:24 — 13:31 AA452 American Airlines
Charlotte — Boston
6h 42m
including layover
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from$205
05:49 — 12:21
05:49 — 08:43 AA2523 American Airlines
Chicago — Charlotte
1h 22m stop
10:05 — 12:21 AA1320 American Airlines
Charlotte — Boston
5h 32m
including layover
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from$205
07:00 — 12:04
07:00 — 09:47 AA2378 American Airlines
Chicago — Washington D.C.
43m stop
10:30 — 12:04 AA2129 American Airlines
Washington D.C. — Boston
4h 4m
including layover
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from$207
08:18 — 13:52
08:18 — 11:08 AA985 American Airlines
Chicago — Washington D.C.
1h 22m stop
12:30 — 13:52 AA2142 American Airlines
Washington D.C. — Boston
4h 34m
including layover
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from$207
09:06 — 14:54
09:06 — 12:00 AA1002 American Airlines
Chicago — Washington D.C.
1h 30m stop
13:30 — 14:54 AA2119 American Airlines
Washington D.C. — Boston
4h 48m
including layover
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from$207
09:25 — 15:25
09:25 — 11:37 UA302 United Airlines
Chicago — Cleveland
2h 3m stop
13:40 — 15:25 UA4267 United Airlines
Cleveland — Boston
5h
including layover
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from$200
10:40 — 17:11
10:40 — 13:37 AA1668 American Airlines
Chicago — Charlotte
1h 23m stop
15:00 — 17:11 AA2801 American Airlines
Charlotte — Boston
5h 31m
including layover
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from$205
12:23 — 18:00
12:23 — 15:18 AA2296 American Airlines
Chicago — Washington D.C.
1h 12m stop
16:30 — 18:00 AA2120 American Airlines
Washington D.C. — Boston
4h 37m
including layover
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from$207
13:37 — 19:07
13:37 — 16:29 AA1486 American Airlines
Chicago — Washington D.C.
1h 1m stop
17:30 — 19:07 AA2116 American Airlines
Washington D.C. — Boston
4h 30m
including layover
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from$210
13:37 — 19:08
13:37 — 16:29 AA1486 American Airlines
Chicago — Washington D.C.
1h 1m stop
17:30 — 19:08 AA4763 American Airlines
Washington D.C. — Boston
4h 31m
including layover
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from$276
13:41 — 18:36
13:41 — 16:23 UA498 United Airlines
Chicago — Washington D.C.
42m stop
17:05 — 18:36 UA822 United Airlines
Washington D.C. — Boston
3h 55m
including layover
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from$199
14:23 — 19:31
14:23 — 16:38 UA1850 United Airlines
Chicago — Cleveland
1h 8m stop
17:46 — 19:31 UA4051 United Airlines
Cleveland — Boston
4h 8m
including layover
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from$200
16:21 — 22:32
16:21 — 19:11 DL1116 Delta Air Lines Inc.
Chicago — Atlanta
47m stop
19:58 — 22:32 DL2100 Delta Air Lines Inc.
Atlanta — Boston
5h 11m
including layover
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from$305
17:08 — 22:27
17:08 — 20:00 AA2499 American Airlines
Chicago — Washington D.C.
1h stop
21:00 — 22:27 AA2150 American Airlines
Washington D.C. — Boston
4h 19m
including layover
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from$210
17:50 — 23:46
17:50 — 20:41 UA225 United Airlines
Chicago — Washington D.C.
1h 34m stop
22:15 — 23:46 UA352 United Airlines
Washington D.C. — Boston
4h 56m
including layover
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from$199
17:55 — 23:10
17:55 — 21:06 UA1997 United Airlines
Chicago — Newark
53m stop
21:59 — 23:10 UA2062 United Airlines
Newark — Boston
4h 15m
including layover
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from$172
18:20 — 00:15
+1 day
18:20 — 21:14 AA354 American Airlines
Chicago — Charlotte
58m stop
22:12 — 00:15 AA1937 American Airlines
Charlotte — Boston
4h 55m
including layover
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from$205
19:35 — 09:38
+1 day
19:35 — 21:53 UA2204 United Airlines
Chicago — Cleveland
9h 57m stop
07:50 — 09:38 UA4079 United Airlines
Cleveland — Boston
13h 3m
including layover
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from$282
21:26 — 07:33
+1 day
21:26 — 00:27 UA1816 United Airlines
Chicago — Newark
6h 3m stop
06:30 — 07:33 UA2294 United Airlines
Newark — Boston
9h 7m
including layover
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from$165
21:26 — 06:11
+1 day
21:26 — 00:27 UA1816 United Airlines
Chicago — Newark
4h 43m stop
05:10 — 06:11 B61280 JetBlue
Newark — Boston
7h 45m
including layover
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from$166
05:49 — 16:47
05:49 — 08:43 AA2523 American Airlines
Chicago — Charlotte
1h 18m stop
10:01 — 12:00 AA429 American Airlines
Charlotte — New York
3h 30m stop
15:30 — 16:47 AA277 American Airlines
New York — Boston
9h 58m
including layover
Find flight
from$192
*Departure and arrival times - local. Updated on April 6, 2020

Flight Information

Below we will explain in detail what the flights cost on the destination from Chicago to Boston depends on and how to choose the most interesting flight option for you.

Distance between Chicago and Boston is 1370 miles. Time difference between the cities is 1h. Airplanes depart 05:25 to 21:26 from 7 Chicago airports and arrive 05:25 to 21:26 to 4 Boston airports . Average flight time is 2h 12m.

  • The fastest flight 2h 11m
  • Average flight time 2h 12m
  • The earliest flight 05:25
  • The latest flight 21:26
  • Distance 852 ml

The cheapest months to travel to Boston are october, november, december, The most expensive months are april.

What is the lowest airfare Chicago to Boston?

The cheapest plane ticket found by our users is $44. This airfare is for economy class on one-way AA2384 flight by American Airlines for April 7, 2020 which leaves O'Hare International in Chicago at 07:15 am and arrives at Boston Logan at 10:26.

Economy class
$44
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Business class
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First class
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Popular Airlines on the Route

The flight Chicago — Boston is served by 4 regular airlines and 1 low-cost airline . Most of the flights on this route are operated by American Airlines - 21 departures per week at the price of from $ 44 . And the most expensive tickets are offered by Delta Air Lines Inc. airline - from $ 305.

Direct flights

There are 14 nonstop flights on the route. The fastest direct flight is AA2384 by American Airlines takes 2h 11m and the cheapest is AA2384 by American Airlines for $44.

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Connecting Flights

There are 23 flights with layovers on the route. The fastest connecting flight is UA498 by United Airlines takes 3h 55m and the cheapest is AA2384 by American Airlines for $165.

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Airports

You can fly from Chicago to Boston from 7 airports (O'Hare International, Midway, Dupage County, Chicago FSS, Merrill C Meigs (closed), Pal-Waukee, Chicago NAS).

Chicago airports

  • O'Hare International-ORD
    from $44
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  • Midway-MDW
    from $305
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  • Dupage County-DPA
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  • Chicago FSS-CHI
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  • Merrill C Meigs (closed)-CGX
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  • Pal-Waukee-PWK
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  • Chicago NAS-NOH
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Boston airports

  • Boston City Heliport-JBC
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  • Boston RT128 Rail-ZRU
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  • Boston South Rail-ZTO
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  • Logan-BOS
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How to book a plane ticket yourself?

How to book an air ticket yourself?
  • Fill in the search parameters — cities of departure and destination, departure and return dates and click «Find flights»
  • Select the best flight that you like. Please, check the airports of departure and arrival. Select the best fare, but pay attention to the following flight details - airports of departure and arrival, flight duration and layovers. Please use filters and sort to find the best flight.
  • Click «Buy» when you are ready — our system will redirect you to the site that sells the selected flight ticket.
  • Fill in all passenger and payment information — passport and contact information, please double check all passengers’ names and make a payment for your itinerary.
  • That's it — you will receive an email with your e-ticket usually within 10 minutes after your flight is confirmed. Please, print the e-ticket and have it with you at the airport. You would need to have only a passport and/or a required form of ID to travel. Please, check your Visa requirements if you travel outside of the United States or Canada.

    To find a plane ticket, please select dates.

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