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).
Direct flights
Check prices for return flight
Best Flights from Chicago to Boston Today
Take a look at the list of non stop flights and flights with layovers from Chicago to Boston with the lowest price of $44. The fastest direct flight takes 2h 11m and the fastest connecting – 3h 55m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $44 | 07:15 Chicago O'Hare International | 10:26 Boston Logan | 2h 11m | American Airlines | AA2384 |
| from $53 | 08:45 Chicago O'Hare International | 11:58 Boston Logan | 2h 13m | American Airlines | AA2723 |
| from $53 | 10:05 Chicago O'Hare International | 13:19 Boston Logan | 2h 14m | American Airlines | AA2264 |
| from $53 | 16:55 Chicago O'Hare International | 20:07 Boston Logan | 2h 12m | American Airlines | AA1251 |
| from $53 | 20:21 Chicago O'Hare International | 23:32 Boston Logan | 2h 11m | American Airlines | AA2682 |
| from $63 | 07:45 Chicago O'Hare International | 10:56 Boston Logan | 2h 11m | United Airlines | UA992 |
| | |||||
| from $63 | 11:58 Chicago O'Hare International | 15:10 Boston Logan | 2h 12m | JetBlue | B6312 |
| from $65 | 08:55 Chicago O'Hare International | 12:06 Boston Logan | 2h 11m | United Airlines | UA1420 |
| from $69 | 11:40 Chicago O'Hare International | 14:51 Boston Logan | 2h 11m | United Airlines | UA532 |
| from $72 | 15:40 Chicago O'Hare International | 18:53 Boston Logan | 2h 13m | United Airlines | UA913 |
| from $77 | 14:00 Chicago O'Hare International | 17:20 Boston Logan | 2h 20m | United Airlines | UA578 |
| from $78 | 13:31 Chicago O'Hare International | 16:43 Boston Logan | 2h 12m | American Airlines | AA1360 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on April 06, 2020
Flight Schedule Chicago (Illinois) to Boston (Massachusetts)
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 |
Find flight
from$44 |
|
|
07:45 — 10:56
|
07:45 — 10:56
UA992
United Airlines
Chicago — Boston
|
2h 11m |
Find flight
from$63 |
|
|
08:45 — 11:58
|
08:45 — 11:58
AA2723
American Airlines
Chicago — Boston
|
2h 13m |
Find flight
from$53 |
|
|
08:55 — 12:06
|
08:55 — 12:06
UA1420
United Airlines
Chicago — Boston
|
2h 11m |
Find flight
from$65 |
|
|
10:05 — 13:19
|
10:05 — 13:19
AA2264
American Airlines
Chicago — Boston
|
2h 14m |
Find flight
from$53 |
|
|
11:40 — 14:51
|
11:40 — 14:51
UA532
United Airlines
Chicago — Boston
|
2h 11m |
Find flight
from$69 |
|
|
11:58 — 15:10
|
11:58 — 15:10
B6312
JetBlue
Chicago — Boston
|
2h 12m |
Find flight
from$63 |
|
|
13:31 — 16:43
|
13:31 — 16:43
AA1360
American Airlines
Chicago — Boston
|
2h 12m |
Find flight
from$78 |
|
|
14:00 — 17:20
|
14:00 — 17:20
UA578
United Airlines
Chicago — Boston
|
2h 20m |
Find flight
from$77 |
|
|
15:40 — 18:53
|
15:40 — 18:53
UA913
United Airlines
Chicago — Boston
|
2h 13m |
Find flight
from$72 |
|
|
16:55 — 20:07
|
16:55 — 20:07
AA1251
American Airlines
Chicago — Boston
|
2h 12m |
Find flight
from$53 |
|
|
18:03 — 21:16
|
18:03 — 21:16
UA790
United Airlines
Chicago — Boston
|
2h 13m |
Find flight
from$102 |
|
|
18:34 — 21:50
|
18:34 — 21:50
AA1172
American Airlines
Chicago — Boston
|
2h 16m |
Find flight
from$85 |
|
|
20:21 — 23:32
|
20:21 — 23:32
AA2682
American Airlines
Chicago — Boston
|
2h 11m |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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 |
Find flight
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
Business class
?
First class
?
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.
- from $44Find
- from $63Find
- from $63Find
See more direct flights
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.
- from $192Find
- from $305Find
- from $165Find
See more connecting flights
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-ORDfrom $44Find
- Midway-MDWfrom $305Find
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Boston airports
- Boston City Heliport-JBCFind
- Boston RT128 Rail-ZRUFind
- Boston South Rail-ZTOFind
- Logan-BOSFind
Airplanes
There are flights to Boston from Chicago by 4 airlines that use 8 aircraft brands. They range from huge modern airplanes to small-sized.
- Airbus A321from $44Find
- Boeing 737-800from $53Find
- Boeing 737-900from $63Find
- Boeing 737from $172Find
- Boeing 757from $199Find
- Airbus A320-100/200from $199Find
- Boeing 737-700from $200Find
- Airbus A319from $305Find
Top Domestic Destinations from Chicago
You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.
- from $79Find
- from $68Find
- from $77Find
- from $74Find
- from $80Find
- from $79Find
- from $76Find
- from $81Find
- from $65Find
- from $61Find
Top International Destinations from Chicago
Our state-of-the art metasearch will definitely provide you with the best airfare on international flights. We’re proud to partner with many reliable travel suppliers located outside the US what gives us an opportunity to offer the most competitive prices on far destinations.
- from $58Find
- from $72Find
- from $57Find
- from $61Find
- from $75Find
- from $60Find
- from $76Find
- from $79Find
- from $71Find
- from $56Find
How to book a plane 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.