Cheap Flights from Chicago, IL to Boston, MA from $62
Return flight: Boston – Chicago
On Cheapflightsplus.com you will find 7 direct and 110 connecting flights from Chicago to Boston. You can compare airfare deals from 8 airlines and multiple travel sites from $62, 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: $62 (one-way), $106 (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 $62. The fastest direct flight takes 2h 19m and the fastest connecting – 4h 21m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $121 | 18:35 Chicago O'Hare International | 21:59 Boston Logan | 2h 24m | United Airlines | UA1989 |
| from $169 | 16:15 Chicago O'Hare International | 19:38 Boston Logan | 2h 23m | United Airlines | UA2658 |
| from $243 | 07:30 Chicago O'Hare International | 10:49 Boston Logan | 2h 19m | United Airlines | UA414 |
| from $62 | 14:28 Chicago O'Hare International | 23:32 Boston Logan | 8h 4m layover 1h 37m - Miami | Spirit Airlines | NK717 NK866 |
| from $62 | 12:00 Chicago O'Hare International | 21:54 Boston Logan | 8h 54m layover 3h 3m - Orlando | Spirit Airlines | NK1686 NK2989 |
| from $62 | 08:00 Chicago O'Hare International | 18:25 Boston Logan | 9h 25m layover 3h 32m - Orlando | Spirit Airlines | NK1686 NK794 |
| from $64 | 16:01 Chicago O'Hare International | 00:27+1 день Boston Logan | 7h 26m layover 1h 25m - Orlando | Frontier Airlines | F93044 F91978 |
| from $69 | 10:59 Chicago O'Hare International | 00:27+1 день Boston Logan | 12h 28m layover 6h 32m - Orlando | Frontier Airlines | F92042 F91978 |
| from $69 | 21:01 Chicago O'Hare International | 11:46+1 день Boston Logan | 13h 45m layover 7h 30m - Dallas | Frontier Airlines | F93243 F93602 |
| from $69 | 08:45 Chicago Midway | 10:46+1 день Boston Logan | 25h 1m layover 19h 14m - Tampa | Frontier Airlines | F91186 F91216 |
| from $69 | 07:00 Chicago O'Hare International | 10:46+1 день Boston Logan | 26h 46m layover 21h 2m - Tampa | Frontier Airlines | F91416 F91216 |
| from $81 | 16:21 Chicago Midway | 00:29+1 день Boston Logan | 7h 8m layover 2h 32m - Atlanta | Frontier Airlines | F92292 F93512 |
| from $87 | 08:13 Chicago O'Hare International | 18:25 Boston Logan | 9h 12m layover 3h 19m - Orlando | Spirit Airlines | NK222 NK794 |
| from $87 | 10:58 Chicago Midway | 00:27+1 день Boston Logan | 12h 29m layover 6h 38m - Orlando | Frontier Airlines | F91458 F91978 |
| from $91 | 07:00 Chicago O'Hare International | 21:54 Boston Logan | 13h 54m layover 4h 9m - Newark 1h 38m - Orlando | Spirit Airlines | NK1680 NK2992 NK2989 |
| from $109 | 05:15 Chicago O'Hare International | 21:54 Boston Logan | 15h 39m layover 5h 42m - Newark 1h 38m - Orlando | Spirit Airlines | NK210 NK2992 NK2989 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on December 21, 2024
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 |
|---|---|---|---|---|
|
07:30 — 10:56
|
07:30 — 10:56
UA1083
United Airlines
Chicago — Boston
|
2h 26m |
Find flight
from$121 |
|
|
07:30 — 10:49
|
07:30 — 10:49
UA414
United Airlines
Chicago — Boston
|
2h 19m |
Find flight
from$243 |
|
|
09:15 — 12:38
|
09:15 — 12:38
UA307
United Airlines
Chicago — Boston
|
2h 23m |
Find flight
from$243 |
|
|
09:20 — 12:46
|
09:20 — 12:46
UA691
United Airlines
Chicago — Boston
|
2h 26m |
Find flight
from$121 |
|
|
16:00 — 19:19
|
16:00 — 19:19
UA2475
United Airlines
Chicago — Boston
|
2h 19m |
Find flight
from$243 |
|
|
16:15 — 19:38
|
16:15 — 19:38
UA2658
United Airlines
Chicago — Boston
|
2h 23m |
Find flight
from$169 |
|
|
18:35 — 21:59
|
18:35 — 21:59
UA1989
United Airlines
Chicago — Boston
|
2h 24m |
Find flight
from$121 |
|
|
05:01 — 11:46
|
05:01 — 08:04
F92112
Frontier Airlines
Chicago — Philadelphia
2h 17m stop
10:21 — 11:46
F93012
Frontier Airlines
Philadelphia — Boston
|
5h 45m including layover |
Find flight
from$91 |
|
|
06:00 — 12:05
|
06:00 — 09:11
UA2343
United Airlines
Chicago — Newark
1h 50m stop
10:55 — 12:07
UA1864
United Airlines
Newark — Boston
|
5h 5m including layover |
Find flight
from$132 |
|
|
06:30 — 16:59
|
06:30 — 10:14
NK715
Spirit Airlines
Chicago — Tampa
3h 44m stop
13:58 — 16:59
NK1371
Spirit Airlines
Tampa — Boston
|
9h 29m including layover |
Find flight
from$131 |
|
|
07:00 — 10:46
+1 day
|
07:00 — 10:43
F91416
Frontier Airlines
Chicago — Tampa
21h 2m stop
07:45 — 10:46
F91216
Frontier Airlines
Tampa — Boston
|
26h 46m including layover |
Find flight
from$69 |
|
|
08:00 — 18:25
|
08:00 — 11:50
NK1686
Spirit Airlines
Chicago — Orlando
3h 32m stop
15:22 — 18:25
NK794
Spirit Airlines
Orlando — Boston
|
9h 25m including layover |
Find flight
from$62 |
|
|
08:45 — 10:46
+1 day
|
06:00 — 09:46
F91186
Frontier Airlines
Chicago — Tampa
19h 14m stop
06:45 — 09:45
F91216
Frontier Airlines
Tampa — Boston
|
25h 1m including layover |
Find flight
from$69 |
|
|
09:10 — 15:41
|
09:10 — 12:28
UA2462
United Airlines
Chicago — Newark
2h 2m stop
14:30 — 15:41
UA2144
United Airlines
Newark — Boston
|
5h 31m including layover |
Find flight
from$132 |
|
|
10:58 — 00:27
+1 day
|
20:20 — 00:16
F91458
Frontier Airlines
Chicago — Orlando
6h 38m stop
21:30 — 00:36
F91978
Frontier Airlines
Orlando — Boston
|
12h 29m including layover |
Find flight
from$87 |
|
|
10:59 — 00:27
+1 day
|
10:59 — 14:51
F92042
Frontier Airlines
Chicago — Orlando
6h 32m stop
21:23 — 00:27
F91978
Frontier Airlines
Orlando — Boston
|
12h 28m including layover |
Find flight
from$69 |
|
|
11:11 — 19:57
|
11:11 — 15:24
NK397
Spirit Airlines
Chicago — Miami
1h 9m stop
16:33 — 19:57
NK888
Spirit Airlines
Miami — Boston
|
7h 46m including layover |
Find flight
from$196 |
|
|
11:51 — 17:12
|
11:51 — 15:06
UA2133
United Airlines
Chicago — Newark
51m stop
16:15 — 17:30
UA1835
United Airlines
Newark — Boston
|
4h 21m including layover |
Find flight
from$132 |
|
|
12:00 — 21:54
|
08:00 — 11:50
NK1686
Spirit Airlines
Chicago — Orlando
3h 3m stop
18:50 — 21:54
NK2989
Spirit Airlines
Orlando — Boston
|
8h 54m including layover |
Find flight
from$62 |
|
|
12:51 — 18:26
|
12:45 — 16:00
UA2238
United Airlines
Chicago — Newark
1h 3m stop
17:15 — 18:33
UA2612
United Airlines
Newark — Boston
|
4h 35m including layover |
Find flight
from$132 |
|
|
13:15 — 19:00
|
13:15 — 16:13
UA2431
United Airlines
Chicago — Washington D.C.
1h 12m stop
17:25 — 19:00
UA688
United Airlines
Washington D.C. — Boston
|
4h 45m including layover |
Find flight
from$132 |
|
|
14:15 — 20:46
|
14:15 — 17:30
UA2115
United Airlines
Chicago — Newark
2h stop
19:30 — 20:46
UA1393
United Airlines
Newark — Boston
|
5h 31m including layover |
Find flight
from$132 |
|
|
14:28 — 23:32
|
14:28 — 18:43
NK717
Spirit Airlines
Chicago — Miami
1h 37m stop
20:20 — 23:32
NK866
Spirit Airlines
Miami — Boston
|
8h 4m including layover |
Find flight
from$62 |
|
|
15:15 — 20:46
|
15:15 — 18:31
UA2649
United Airlines
Chicago — Newark
59m stop
19:30 — 20:46
UA1393
United Airlines
Newark — Boston
|
4h 31m including layover |
Find flight
from$132 |
|
|
15:51 — 23:59
|
15:51 — 18:43
UA2451
United Airlines
Chicago — Washington D.C.
3h 41m stop
22:24 — 23:59
UA755
United Airlines
Washington D.C. — Boston
|
7h 8m including layover |
Find flight
from$132 |
|
|
16:01 — 00:27
+1 day
|
20:26 — 00:29
F93044
Frontier Airlines
Chicago — Orlando
1h 25m stop
21:30 — 00:36
F91978
Frontier Airlines
Orlando — Boston
|
7h 26m including layover |
Find flight
from$64 |
|
|
16:21 — 00:29
+1 day
|
16:21 — 19:28
F92292
Frontier Airlines
Chicago — Atlanta
2h 32m stop
22:00 — 00:29
F93512
Frontier Airlines
Atlanta — Boston
|
7h 8m including layover |
Find flight
from$81 |
|
|
18:14 — 23:59
|
18:08 — 21:00
UA444
United Airlines
Chicago — Washington D.C.
1h 15m stop
22:24 — 23:59
UA755
United Airlines
Washington D.C. — Boston
|
4h 45m including layover |
Find flight
from$132 |
|
|
19:59 — 06:55
+1 day
|
19:59 — 23:12
F91618
Frontier Airlines
Chicago — Philadelphia
6h 18m stop
05:30 — 06:55
F92168
Frontier Airlines
Philadelphia — Boston
|
9h 56m including layover |
Find flight
from$136 |
|
|
20:54 — 12:00
+1 day
|
20:54 — 23:24
F92881
Frontier Airlines
Chicago — Dallas
7h 51m stop
07:15 — 12:00
F93602
Frontier Airlines
Dallas — Boston
|
14h 6m including layover |
Find flight
from$136 |
|
|
21:01 — 11:46
+1 day
|
21:01 — 23:42
F93243
Frontier Airlines
Chicago — Dallas
7h 30m stop
07:12 — 11:46
F93602
Frontier Airlines
Dallas — Boston
|
13h 45m including layover |
Find flight
from$69 |
|
|
05:15 — 21:54
|
05:15 — 08:31
NK210
Spirit Airlines
Chicago — Newark
5h 42m stop
14:13 — 17:12
NK2992
Spirit Airlines
Newark — Orlando
1h 38m stop
18:50 — 21:54
NK2989
Spirit Airlines
Orlando — Boston
|
15h 39m including layover |
Find flight
from$109 |
|
|
07:00 — 21:54
|
07:00 — 10:04
NK1680
Spirit Airlines
Chicago — Newark
4h 9m stop
14:13 — 17:12
NK2992
Spirit Airlines
Newark — Orlando
1h 38m stop
18:50 — 21:54
NK2989
Spirit Airlines
Orlando — Boston
|
13h 54m including layover |
Find flight
from$91 |
|
|
20:52 — 15:13
+1 day
|
20:52 — 00:44
NK1686
Spirit Airlines
Chicago — Orlando
5h 46m stop
06:30 — 07:29
NK1700
Spirit Airlines
Orlando — New Orleans
3h 25m stop
10:54 — 15:13
NK1375
Spirit Airlines
New Orleans — Boston
|
17h 21m including layover |
Find flight
from$147 |
|
*Departure and arrival times - local. Updated on December 21, 2024
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 05:00 to 21:45 from 7 Chicago airports and arrive 05:00 to 21:45 to 4 Boston airports. Average flight time is 2h 23m.
- The fastest flight 2h 19m
- Average flight time 2h 23m
- The earliest flight 05:00
- The latest flight 21:45
- Distance 852 ml
The cheapest months to travel to Boston are january (from 62 $), december (from 68 $), november (from 77 $).
The most expensive months are february (from 87 $), november (from 77 $), december (from 68 $).
What is the lowest airfare Chicago to Boston?
The cheapest plane ticket found by our users is $62. This airfare is for economy class on one-way NK1686 flight by Spirit Airlines for January 22, 2025 which leaves O'Hare International in Chicago at 12:00 am and arrives at Boston Logan at 21:54.
Economy class
$62
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Boston is served by 8 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 5 departures per week at the price of from $ 219 . And the most expensive tickets are offered by SWISS International Air Lines airline - from $ 5980.
Direct flights
There are 7 nonstop flights on the route. The fastest direct flight is UA414 by United Airlines takes 2h 19m and the cheapest is NK1686 by Spirit Airlines for $121.
- from $121Find
See more direct flights
Connecting Flights
There are 110 flights with layovers on the route. The fastest connecting flight is UA2133 by United Airlines takes 4h 21m and the cheapest is NK1686 by Spirit Airlines for $62.
- from $219Find
- from $64Find
- from $314Find
- from $132Find
- from $62Find
- TK - Turkish Airlinesfrom $1135Find
- LX - SWISS International Air Linesfrom $5980Find
- TS - Air Transatfrom $347Find
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 $62Find
- Midway-MDWfrom $69Find
- 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 8 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.
- from $508Find
- from $63Find
- from $181Find
- from $62Find
- from $74Find
- from $70Find
- from $59Find
- from $76Find
- from $66Find
- 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 $60Find
- from $58Find
- from $61Find
- from $72Find
- from $59Find
- from $72Find
- from $79Find
- from $61Find
- from $628Find
- from $74Find
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.