Cheap Flights from Chicago, IL to Boston, MA from $53
Return flight: Boston – Chicago
On Cheapflightsplus.com you will find 14 direct and 321 connecting flights from Chicago to Boston. You can compare airfare deals from 9 airlines and multiple travel sites from $53, 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: $53 (one-way), $91 (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 $53. The fastest direct flight takes 2h 26m and the fastest connecting – 4h 20m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $79 | 06:30 Chicago O'Hare International | 09:56 Boston Logan | 2h 26m | United Airlines | UA2104 |
| from $79 | 07:49 Chicago O'Hare International | 11:16 Boston Logan | 2h 27m | United Airlines | UA2067 |
| from $79 | 19:45 Chicago O'Hare International | 23:12 Boston Logan | 2h 27m | United Airlines | UA1129 |
| from $79 | 21:32 Chicago O'Hare International | 00:59+1 день Boston Logan | 2h 27m | United Airlines | UA1779 |
| from $79 | 14:28 Chicago O'Hare International | 18:06 Boston Logan | 2h 38m | United Airlines | UA2138 |
| from $103 | 17:57 Chicago O'Hare International | 21:28 Boston Logan | 2h 31m | United Airlines | UA1531 |
| from $125 | 13:12 Chicago O'Hare International | 16:43 Boston Logan | 2h 31m | United Airlines | UA2022 |
| from $53 | 07:15 Chicago O'Hare International | 15:35 Boston Logan | 7h 20m layover 1h 27m - Orlando | Spirit Airlines | NK3200 NK3796 |
| from $53 | 15:29 Chicago O'Hare International | 00:39+1 день Boston Logan | 8h 10m layover 1h 46m - Miami | Spirit Airlines | NK867 NK616 |
| from $64 | 16:34 Chicago O'Hare International | 00:43+1 день Boston Logan | 7h 9m layover 1h 3m - Tampa | Frontier Airlines | F91416 F91216 |
| from $66 | 11:11 Chicago O'Hare International | 21:54 Boston Logan | 9h 43m layover 5h 35m - Myrtle Beach | Spirit Airlines | NK1819 NK1005 |
| from $67 | 11:21 Chicago O'Hare International | 19:21 Boston Logan | 7h 0m layover 0h 45m - Dallas | Spirit Airlines | NK1633 NK1838 |
| from $72 | 16:37 Chicago O'Hare International | 08:35+1 день Boston Logan | 14h 58m layover 8h 51m - Orlando | Frontier Airlines | F92792 F93348 |
| from $72 | 08:35 Chicago Midway | 08:35+1 день Boston Logan | 23h 0m layover 17h 10m - Orlando | Frontier Airlines | F91458 F93348 |
| from $88 | 17:10 Chicago O'Hare International | 15:35+1 день Boston Logan | 21h 25m layover 9h 17m - Newark 3h 56m - Orlando | Spirit Airlines | NK328 NK1801 NK3796 |
| from $103 | 15:36 Chicago O'Hare International | 23:03+1 день Boston Logan | 30h 27m layover 21h 16m - Nashville 2h 36m - Orlando | Spirit Airlines | NK1184 NK1747 NK1452 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 03, 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$79 |
|
|
07:49 — 11:16
|
07:49 — 11:16
UA2067
United Airlines
Chicago — Boston
|
2h 27m |
Find flight
from$79 |
|
|
09:07 — 12:42
|
09:07 — 12:42
UA1346
United Airlines
Chicago — Boston
|
2h 35m |
Find flight
from$81 |
|
|
09:13 — 12:48
|
09:13 — 12:48
UA536
United Airlines
Chicago — Boston
|
2h 35m |
Find flight
from$80 |
|
|
13:12 — 16:43
|
13:12 — 16:43
UA2022
United Airlines
Chicago — Boston
|
2h 31m |
Find flight
from$125 |
|
|
13:30 — 17:02
|
13:30 — 17:02
UA1262
United Airlines
Chicago — Boston
|
2h 32m |
Find flight
from$81 |
|
|
14:15 — 17:46
|
14:15 — 17:46
UA1693
United Airlines
Chicago — Boston
|
2h 31m |
Find flight
from$83 |
|
|
14:15 — 17:46
|
14:15 — 17:46
UA664
United Airlines
Chicago — Boston
|
2h 31m |
Find flight
from$125 |
|
|
14:28 — 18:06
|
14:28 — 18:06
UA2138
United Airlines
Chicago — Boston
|
2h 38m |
Find flight
from$79 |
|
|
14:28 — 18:06
|
14:28 — 18:06
UA2370
United Airlines
Chicago — Boston
|
2h 38m |
Find flight
from$79 |
|
|
17:57 — 21:28
|
17:57 — 21:28
UA1531
United Airlines
Chicago — Boston
|
2h 31m |
Find flight
from$103 |
|
|
18:04 — 21:35
|
18:04 — 21:35
UA1989
United Airlines
Chicago — Boston
|
2h 31m |
Find flight
from$81 |
|
|
19:45 — 23:12
|
19:45 — 23:12
UA1129
United Airlines
Chicago — Boston
|
2h 27m |
Find flight
from$79 |
|
|
21:32 — 00:59
+1 day
|
21:32 — 00:59
UA1779
United Airlines
Chicago — Boston
|
2h 27m |
Find flight
from$79 |
|
|
05:05 — 19:34
|
05:05 — 09:12
NK1
Spirit Airlines
Chicago — Miami
7h 3m stop
16:15 — 19:34
NK1230
Spirit Airlines
Miami — Boston
|
13h 29m including layover |
Find flight
from$82 |
|
|
05:05 — 00:39
+1 day
|
05:05 — 09:10
NK19
Spirit Airlines
Chicago — Miami
12h 15m stop
21:25 — 00:39
NK616
Spirit Airlines
Miami — Boston
|
18h 34m including layover |
Find flight
from$105 |
|
|
06:00 — 13:40
|
06:00 — 09:10
UA1658
United Airlines
Chicago — Newark
3h 12m stop
15:04 — 16:19
UA593
United Airlines
Newark — Boston
|
6h 40m including layover |
Find flight
from$99 |
|
|
07:15 — 15:35
|
07:15 — 11:03
NK3200
Spirit Airlines
Chicago — Orlando
1h 27m stop
12:30 — 15:35
NK3796
Spirit Airlines
Orlando — Boston
|
7h 20m including layover |
Find flight
from$53 |
|
|
08:35 — 08:35
+1 day
|
08:35 — 12:20
F91458
Frontier Airlines
Chicago — Orlando
17h 10m stop
05:30 — 08:35
F93348
Frontier Airlines
Orlando — Boston
|
23h including layover |
Find flight
from$72 |
|
|
08:47 — 15:32
|
08:45 — 12:09
UA2691
United Airlines
Chicago — Newark
2h 5m stop
15:00 — 16:19
UA577
United Airlines
Newark — Boston
|
5h 45m including layover |
Find flight
from$99 |
|
|
10:00 — 23:03
|
10:00 — 13:39
NK1113
Spirit Airlines
Chicago — Orlando
6h 16m stop
19:55 — 23:03
NK1452
Spirit Airlines
Orlando — Boston
|
12h 3m including layover |
Find flight
from$97 |
|
|
10:31 — 09:46
+1 day
|
10:31 — 13:09
G41846
Allegiant Air
Chicago — Fletcher
18h 26m stop
07:35 — 09:46
G4269
Allegiant Air
Fletcher — Boston
|
22h 15m including layover |
Find flight
from$85 |
|
|
11:11 — 21:54
|
11:11 — 14:11
NK1819
Spirit Airlines
Chicago — Myrtle Beach
5h 35m stop
19:46 — 21:54
NK1005
Spirit Airlines
Myrtle Beach — Boston
|
9h 43m including layover |
Find flight
from$66 |
|
|
11:21 — 19:21
|
11:21 — 13:51
NK1633
Spirit Airlines
Chicago — Dallas
45m stop
14:36 — 19:21
NK1838
Spirit Airlines
Dallas — Boston
|
7h including layover |
Find flight
from$67 |
|
|
13:11 — 09:11
+1 day
|
13:11 — 15:49
G41846
Allegiant Air
Chicago — Fletcher
15h 11m stop
07:00 — 09:11
G4228
Allegiant Air
Fletcher — Boston
|
19h including layover |
Find flight
from$81 |
|
|
15:29 — 00:39
+1 day
|
15:29 — 19:39
NK867
Spirit Airlines
Chicago — Miami
1h 46m stop
21:25 — 00:39
NK616
Spirit Airlines
Miami — Boston
|
8h 10m including layover |
Find flight
from$53 |
|
|
16:34 — 00:43
+1 day
|
07:00 — 10:43
F91416
Frontier Airlines
Chicago — Tampa
1h 3m stop
07:45 — 10:46
F91216
Frontier Airlines
Tampa — Boston
|
7h 9m including layover |
Find flight
from$64 |
|
|
16:37 — 08:35
+1 day
|
09:58 — 13:42
F92792
Frontier Airlines
Chicago — Orlando
8h 51m stop
05:30 — 08:40
F93348
Frontier Airlines
Orlando — Boston
|
14h 58m including layover |
Find flight
from$72 |
|
|
18:15 — 09:19
+1 day
|
18:15 — 19:55
SY260
Sun Country Airlines
Chicago — Minneapolis
9h 41m stop
05:36 — 09:19
SY249
Sun Country Airlines
Minneapolis — Boston
|
14h 4m including layover |
Find flight
from$102 |
|
|
19:39 — 15:35
+1 day
|
19:39 — 23:32
NK507
Spirit Airlines
Chicago — Orlando
12h 58m stop
12:30 — 15:35
NK3796
Spirit Airlines
Orlando — Boston
|
18h 56m including layover |
Find flight
from$98 |
|
|
20:27 — 07:59
+1 day
|
20:27 — 23:53
F92112
Frontier Airlines
Chicago — Philadelphia
6h 37m stop
06:30 — 07:59
F92168
Frontier Airlines
Philadelphia — Boston
|
10h 32m including layover |
Find flight
from$91 |
|
|
21:12 — 08:35
+1 day
|
21:12 — 00:53
F93854
Frontier Airlines
Chicago — Orlando
4h 27m stop
05:30 — 08:40
F93348
Frontier Airlines
Orlando — Boston
|
10h 23m including layover |
Find flight
from$90 |
|
|
15:36 — 23:03
+1 day
|
15:36 — 17:05
NK1184
Spirit Airlines
Chicago — Nashville
21h 16m stop
14:21 — 17:19
NK1747
Spirit Airlines
Nashville — Orlando
2h 36m stop
19:55 — 23:03
NK1452
Spirit Airlines
Orlando — Boston
|
30h 27m including layover |
Find flight
from$103 |
|
|
17:10 — 15:35
+1 day
|
17:10 — 20:28
NK328
Spirit Airlines
Chicago — Newark
9h 17m stop
05:45 — 08:34
NK1801
Spirit Airlines
Newark — Orlando
3h 56m stop
12:30 — 15:35
NK3796
Spirit Airlines
Orlando — Boston
|
21h 25m including layover |
Find flight
from$88 |
|
|
17:10 — 18:18
+1 day
|
17:10 — 20:28
NK328
Spirit Airlines
Chicago — Newark
16h 50m stop
13:18 — 15:13
NK3021
Spirit Airlines
Newark — Myrtle Beach
55m stop
16:08 — 18:18
NK138
Spirit Airlines
Myrtle Beach — Boston
|
24h 8m including layover |
Find flight
from$88 |
|
|
20:12 — 15:35
+1 day
|
20:12 — 23:31
NK919
Spirit Airlines
Chicago — Newark
6h 14m stop
05:45 — 08:34
NK1801
Spirit Airlines
Newark — Orlando
3h 56m stop
12:30 — 15:35
NK3796
Spirit Airlines
Orlando — Boston
|
18h 23m including layover |
Find flight
from$92 |
|
*Departure and arrival times - local. Updated on July 3, 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 22:15 from 7 Chicago airports and arrive 05:05 to 22:15 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 22:15
- Distance 852 ml
The cheapest months to travel to Boston are october (from 71 $), january (from 86 $), august (from 89 $).
The most expensive months are november (from 262 $), june (from 107 $), september (from 99 $).
What is the lowest airfare Chicago to Boston?
The cheapest plane ticket found by our users is $53. This airfare is for economy class on one-way NK867 flight by Spirit Airlines for October 7, 2025 which leaves O'Hare International in Chicago at 15:29 am and arrives at Boston Logan at 00:39.
Economy class
$53
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Boston is served by 9 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by United Airlines - 159 departures per week at the price of from $ 79 . And the most expensive tickets are offered by Turkish Airlines airline - from $ 2019.
Direct flights
There are 14 nonstop flights on the route. The fastest direct flight is UA2104 by United Airlines takes 2h 26m and the cheapest is NK867 by Spirit Airlines for $79.
- from $79Find
See more direct flights
Connecting Flights
There are 321 flights with layovers on the route. The fastest connecting flight is UA1068 by United Airlines takes 4h 20m and the cheapest is NK867 by Spirit Airlines for $53.
- from $88Find
- from $53Find
- AS - Alaska Airlinesfrom $159Find
- F9 - Frontier Airlinesfrom $64Find
- SY - Sun Country Airlinesfrom $102Find
- TK - Turkish Airlinesfrom $2019Find
- AY - Finnairfrom $798Find
- HA - Hawaiian Airlinesfrom $184Find
- G4 - Allegiant Airfrom $81Find
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 $53Find
- Midway-MDWfrom $72Find
- 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 9 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
- from $72Find
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- from $79Find
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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.