Cheap Flights from Chicago, IL to Boston, MA from $104
Return flight: Boston – Chicago
On Cheapflightsplus.com you will find 8 direct and 63 connecting flights from Chicago to Boston. You can compare airfare deals from 6 airlines and multiple travel sites from $104, 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: $104 (one-way), $178 (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 $104. The fastest direct flight takes 2h 26m and the fastest connecting – 4h 23m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $104 | 09:13 Chicago O'Hare International | 12:48 Boston Logan | 2h 35m | United Airlines | UA536 |
| from $106 | 06:30 Chicago O'Hare International | 09:56 Boston Logan | 2h 26m | United Airlines | UA2104 |
| from $134 | 17:57 Chicago O'Hare International | 21:28 Boston Logan | 2h 31m | United Airlines | UA1531 |
| from $163 | 13:12 Chicago O'Hare International | 16:43 Boston Logan | 2h 31m | United Airlines | UA2022 |
| from $163 | 14:15 Chicago O'Hare International | 17:46 Boston Logan | 2h 31m | United Airlines | UA664 |
| from $268 | 11:05 Chicago O'Hare International | 14:40 Boston Logan | 2h 35m | United Airlines | UA399 |
| from $400 | 21:15 Chicago O'Hare International | 00:45+1 день Boston Logan | 2h 30m | United Airlines | UA1779 |
| from $474 | 15:48 Chicago O'Hare International | 19:19 Boston Logan | 2h 31m | United Airlines | UA1677 |
| from $138 | 07:15 Chicago O'Hare International | 13:24 Boston Logan | 5h 9m layover 1h 37m - Newark | United Airlines | UA563 UA408 |
| from $138 | 06:00 Chicago O'Hare International | 13:24 Boston Logan | 6h 24m layover 2h 55m - Newark | United Airlines | UA1658 UA408 |
| from $138 | 14:20 Chicago O'Hare International | 23:08 Boston Logan | 7h 48m layover 3h 58m - Newark | United Airlines | UA2649 UA1395 |
| from $144 | 17:55 Chicago O'Hare International | 23:57 Boston Logan | 5h 2m layover 1h 23m - Washington D.C. | United Airlines | UA2677 UA755 |
| from $217 | 10:35 Chicago O'Hare International | 16:28 Boston Logan | 4h 53m layover 1h 18m - Newark | United Airlines | UA1126 UA2033 |
| from $247 | 20:12 Chicago O'Hare International | 11:18+1 день Boston Logan | 14h 6m layover 7h 45m - Miami | Spirit Airlines | NK2126 NK2300 |
| from $249 | 17:03 Chicago O'Hare International | 23:08 Boston Logan | 5h 5m layover 1h 15m - Newark | United Airlines | UA1276 UA1395 |
| from $269 | 21:31 Chicago O'Hare International | 18:55+1 день Boston Logan | 20h 24m layover 16h 44m - Washington D.C. | United Airlines | UA276 UA688 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on September 01, 2025
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 |
|---|---|---|---|---|
|
06:30 — 09:56
|
06:30 — 09:56
UA2104
United Airlines
Chicago — Boston
|
2h 26m |
Find flight
from$106 |
|
|
09:13 — 12:48
|
09:13 — 12:48
UA536
United Airlines
Chicago — Boston
|
2h 35m |
Find flight
from$104 |
|
|
11:05 — 14:40
|
11:05 — 14:40
UA399
United Airlines
Chicago — Boston
|
2h 35m |
Find flight
from$268 |
|
|
13:12 — 16:43
|
13:12 — 16:43
UA2022
United Airlines
Chicago — Boston
|
2h 31m |
Find flight
from$163 |
|
|
14:15 — 17:46
|
14:15 — 17:46
UA664
United Airlines
Chicago — Boston
|
2h 31m |
Find flight
from$163 |
|
|
15:48 — 19:19
|
15:48 — 19:19
UA1677
United Airlines
Chicago — Boston
|
2h 31m |
Find flight
from$474 |
|
|
17:57 — 21:28
|
17:57 — 21:28
UA1531
United Airlines
Chicago — Boston
|
2h 31m |
Find flight
from$134 |
|
|
21:15 — 00:45
+1 day
|
21:15 — 00:45
UA1779
United Airlines
Chicago — Boston
|
2h 30m |
Find flight
from$400 |
|
|
05:05 — 11:18
+1 day
|
05:05 — 09:13
NK1
Spirit Airlines
Chicago — Miami
22h 52m stop
08:05 — 11:18
NK2300
Spirit Airlines
Miami — Boston
|
29h 13m including layover |
Find flight
from$401 |
|
|
06:00 — 13:24
|
06:00 — 09:15
UA1658
United Airlines
Chicago — Newark
2h 55m stop
12:10 — 13:24
UA408
United Airlines
Newark — Boston
|
6h 24m including layover |
Find flight
from$138 |
|
|
07:15 — 13:24
|
07:15 — 10:33
UA563
United Airlines
Chicago — Newark
1h 37m stop
12:10 — 13:24
UA408
United Airlines
Newark — Boston
|
5h 9m including layover |
Find flight
from$138 |
|
|
07:15 — 15:14
|
07:15 — 10:33
UA563
United Airlines
Chicago — Newark
3h 27m stop
14:00 — 15:14
UA333
United Airlines
Newark — Boston
|
6h 59m including layover |
Find flight
from$487 |
|
|
08:50 — 14:13
|
08:50 — 11:55
UA2029
United Airlines
Chicago — Washington D.C.
40m stop
12:35 — 14:13
UA1709
United Airlines
Washington D.C. — Boston
|
4h 23m including layover |
Find flight
from$278 |
|
|
08:50 — 17:34
|
08:50 — 11:55
UA2029
United Airlines
Chicago — Washington D.C.
4h stop
15:55 — 17:34
UA315
United Airlines
Washington D.C. — Boston
|
7h 44m including layover |
Find flight
from$278 |
|
|
10:35 — 16:28
|
10:35 — 13:52
UA1126
United Airlines
Chicago — Newark
1h 18m stop
15:10 — 16:28
UA2033
United Airlines
Newark — Boston
|
4h 53m including layover |
Find flight
from$217 |
|
|
10:43 — 17:34
|
10:43 — 13:49
UA1030
United Airlines
Chicago — Washington D.C.
2h 6m stop
15:55 — 17:34
UA315
United Airlines
Washington D.C. — Boston
|
5h 51m including layover |
Find flight
from$278 |
|
|
12:50 — 23:57
|
12:50 — 15:52
UA1377
United Airlines
Chicago — Washington D.C.
6h 26m stop
22:18 — 23:57
UA755
United Airlines
Washington D.C. — Boston
|
10h 7m including layover |
Find flight
from$273 |
|
|
14:20 — 23:08
|
14:20 — 17:47
UA2649
United Airlines
Chicago — Newark
3h 58m stop
21:45 — 23:08
UA1395
United Airlines
Newark — Boston
|
7h 48m including layover |
Find flight
from$138 |
|
|
15:52 — 11:14
+1 day
|
15:52 — 18:20
G43053
Allegiant Air
Chicago — Knoxville
14h 40m stop
09:00 — 11:14
G41430
Allegiant Air
Knoxville — Boston
|
18h 22m including layover |
Find flight
from$289 |
|
|
17:55 — 23:57
|
17:56 — 20:55
UA2677
United Airlines
Chicago — Washington D.C.
1h 23m stop
22:18 — 23:59
UA755
United Airlines
Washington D.C. — Boston
|
5h 2m including layover |
Find flight
from$144 |
|
|
18:05 — 08:09
+1 day
|
18:05 — 21:33
UA534
United Airlines
Chicago — Newark
9h 22m stop
06:55 — 08:09
UA2669
United Airlines
Newark — Boston
|
13h 4m including layover |
Find flight
from$583 |
|
|
19:35 — 08:09
+1 day
|
19:35 — 22:59
UA2362
United Airlines
Chicago — Newark
7h 56m stop
08:30 — 09:49
UA2669
United Airlines
Newark — Boston
|
11h 34m including layover |
Find flight
from$286 |
|
|
20:12 — 11:18
+1 day
|
20:12 — 00:20
NK2126
Spirit Airlines
Chicago — Miami
7h 45m stop
08:05 — 11:18
NK2300
Spirit Airlines
Miami — Boston
|
14h 6m including layover |
Find flight
from$247 |
|
|
21:31 — 18:55
+1 day
|
21:31 — 00:30
UA276
United Airlines
Chicago — Washington D.C.
16h 44m stop
17:33 — 19:20
UA688
United Airlines
Washington D.C. — Boston
|
20h 24m including layover |
Find flight
from$269 |
|
|
05:05 — 22:34
|
05:05 — 09:13
NK1
Spirit Airlines
Chicago — Miami
2h 57m stop
12:10 — 15:11
NK2239
Spirit Airlines
Miami — Detroit
5h 24m stop
20:35 — 22:34
NK2152
Spirit Airlines
Detroit — Boston
|
16h 29m including layover |
Find flight
from$442 |
|
|
09:10 — 22:34
|
09:10 — 12:06
F93088
Frontier Airlines
Chicago — Baltimore
2h 24m stop
14:30 — 16:05
NK509
Spirit Airlines
Baltimore — Detroit
4h 30m stop
20:35 — 22:34
NK2152
Spirit Airlines
Detroit — Boston
|
12h 24m including layover |
Find flight
from$431 |
|
|
11:21 — 11:18
+1 day
|
11:21 — 14:11
NK2493
Spirit Airlines
Chicago — Atlanta
6h 51m stop
21:02 — 22:57
NK2269
Spirit Airlines
Atlanta — Miami
9h 8m stop
08:05 — 11:18
NK2300
Spirit Airlines
Miami — Boston
|
22h 57m including layover |
Find flight
from$430 |
|
|
13:47 — 09:39
+1 day
|
13:47 — 17:03
F93142
Frontier Airlines
Chicago — Charlotte
4h 38m stop
21:41 — 23:35
F92451
Frontier Airlines
Charlotte — Orlando
6h 55m stop
06:30 — 09:39
NK2443
Spirit Airlines
Orlando — Boston
|
18h 52m including layover |
Find flight
from$425 |
|
|
15:25 — 09:39
+1 day
|
15:25 — 17:53
F92999
Frontier Airlines
Chicago — Dallas
2h 1m stop
19:54 — 23:38
F92886
Frontier Airlines
Dallas — Orlando
6h 52m stop
06:30 — 09:39
NK2443
Spirit Airlines
Orlando — Boston
|
17h 14m including layover |
Find flight
from$435 |
|
|
19:46 — 11:18
+1 day
|
19:46 — 23:52
F92792
Frontier Airlines
Chicago — Orlando
6h 28m stop
06:20 — 07:33
NK2205
Spirit Airlines
Orlando — Miami
32m stop
08:05 — 11:18
NK2300
Spirit Airlines
Miami — Boston
|
14h 32m including layover |
Find flight
from$385 |
|
|
20:12 — 13:48
+1 day
|
20:12 — 00:20
NK2126
Spirit Airlines
Chicago — Miami
6h 40m stop
07:00 — 08:04
NK2212
Spirit Airlines
Miami — Orlando
2h 39m stop
10:43 — 13:48
NK2178
Spirit Airlines
Orlando — Boston
|
16h 36m including layover |
Find flight
from$620 |
|
|
21:45 — 09:39
+2 days
|
21:45 — 23:54
F92145
Frontier Airlines
Chicago — Las Vegas
15h 21m stop
15:15 — 23:21
F93914
Frontier Airlines
Las Vegas — Orlando
7h 9m stop
06:30 — 09:39
NK2443
Spirit Airlines
Orlando — Boston
|
34h 54m including layover |
Find flight
from$357 |
|
*Departure and arrival times - local. Updated on September 1, 2025
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 05:05 to 23:45 from 7 Chicago airports and arrive 05:05 to 23:45 to 4 Boston airports. Average flight time is 2h 31m.
- The fastest flight 2h 26m
- Average flight time 2h 31m
- The earliest flight 05:05
- The latest flight 23:45
- Distance 852 ml
The cheapest months to travel to Boston are may (from 92 $), september (from 92 $), july (from 103 $).
The most expensive months are november (from 4 115 $), october (from 106 $), june (from 104 $).
What is the lowest airfare Chicago to Boston?
The cheapest plane ticket found by our users is $104. This airfare is for economy class on one-way UA536 flight by United Airlines for August 25, 2025 which leaves O'Hare International in Chicago at 09:13 am and arrives at Boston Logan at 12:48.
Economy class
$104
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Boston is served by 6 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by United Airlines - 38 departures per week at the price of from $ 104 . And the most expensive tickets are offered by Turkish Airlines airline - from $ 4578.
Direct flights
There are 8 nonstop flights on the route. The fastest direct flight is UA2104 by United Airlines takes 2h 26m and the cheapest is UA536 by United Airlines for $104.
- from $104Find
See more direct flights
Connecting Flights
There are 63 flights with layovers on the route. The fastest connecting flight is UA2029 by United Airlines takes 4h 23m and the cheapest is UA536 by United Airlines for $138.
- from $138Find
- from $247Find
- F9 - Frontier Airlinesfrom $357Find
- TK - Turkish Airlinesfrom $4578Find
- AY - Finnairfrom $1928Find
- G4 - Allegiant Airfrom $289Find
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 $104Find
- Midway-MDWfrom $289Find
- 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 6 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top Domestic Destinations from Chicago
You may also consider searching for discounted plane tickets to some other popular places from Chicago within United States.
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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 $60Find
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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.