Cheap Flights from Chicago, IL to Boston, MA from $102
Return flight: Boston – Chicago
On Cheapflightsplus.com you will find 12 direct and 164 connecting flights from Chicago to Boston. You can compare airfare deals from 8 airlines and multiple travel sites from $102, 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: $102 (one-way), $175 (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 $102. The fastest direct flight takes 2h 24m and the fastest connecting – 4h 24m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $129 | 18:25 Chicago O'Hare International | 21:57 Boston Logan | 2h 32m | United Airlines | UA1989 |
| from $140 | 21:32 Chicago O'Hare International | 00:59+1 день Boston Logan | 2h 27m | United Airlines | UA1779 |
| from $167 | 12:50 Chicago O'Hare International | 16:17 Boston Logan | 2h 27m | United Airlines | UA1532 |
| from $200 | 13:55 Chicago O'Hare International | 17:19 Boston Logan | 2h 24m | United Airlines | UA580 |
| from $239 | 06:00 Chicago O'Hare International | 09:26 Boston Logan | 2h 26m | United Airlines | UA2104 |
| from $276 | 07:27 Chicago O'Hare International | 10:54 Boston Logan | 2h 27m | United Airlines | UA2067 |
| from $102 | 16:15 Chicago O'Hare International | 00:44+1 день Boston Logan | 7h 29m layover 1h 15m - Orlando | Frontier Airlines | F93044 F93348 |
| from $114 | 10:34 Chicago Midway | 09:47+1 день Boston Logan | 22h 13m layover 18h 24m - Fletcher | Allegiant Air | G4218 G4232 |
| from $117 | 05:05 Chicago O'Hare International | 14:44 Boston Logan | 8h 39m layover 2h 23m - Miami | Spirit Airlines | NK2 NK2126 |
| from $118 | 16:00 Chicago Midway | 09:34+1 день Boston Logan | 16h 34m layover 10h 37m - Tampa | Frontier Airlines | F91186 F91216 |
| from $118 | 06:00 Chicago O'Hare International | 11:10+1 день Boston Logan | 28h 10m layover 23h 55m - Raleigh | Frontier Airlines | F93352 F93058 |
| from $124 | 09:12 Chicago Midway | 12:01+1 день Boston Logan | 25h 49m layover 20h 37m - Fort Walton Beach | Allegiant Air | G43081 G41443 |
| from $134 | 15:40 Chicago O'Hare International | 22:26 Boston Logan | 5h 46m layover 1h 51m - Newark | United Airlines | UA2216 UA1393 |
| from $153 | 16:34 Chicago O'Hare International | 00:43+1 день Boston Logan | 7h 9m layover 1h 3m - Tampa | Frontier Airlines | F91416 F91216 |
| from $169 | 13:59 Chicago O'Hare International | 08:41+1 день Boston Logan | 17h 42m layover 1h 5m - Myrtle Beach 10h 44m - Detroit | Spirit Airlines | NK2521 NK2475 NK2149 |
| from $197 | 12:41 Chicago O'Hare International | 08:41+1 день Boston Logan | 19h 0m layover 4h 42m - Miami 6h 18m - Detroit | Spirit Airlines | NK2187 NK2902 NK2149 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on May 13, 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 |
|---|---|---|---|---|
|
06:00 — 09:26
|
06:00 — 09:26
UA2104
United Airlines
Chicago — Boston
|
2h 26m |
Find flight
from$239 |
|
|
07:27 — 10:54
|
07:27 — 10:54
UA2067
United Airlines
Chicago — Boston
|
2h 27m |
Find flight
from$276 |
|
|
09:20 — 12:48
|
09:20 — 12:48
UA721
United Airlines
Chicago — Boston
|
2h 28m |
Find flight
from$239 |
|
|
10:35 — 14:03
|
10:35 — 14:03
UA399
United Airlines
Chicago — Boston
|
2h 28m |
Find flight
from$266 |
|
|
12:50 — 16:17
|
12:50 — 16:17
UA1532
United Airlines
Chicago — Boston
|
2h 27m |
Find flight
from$167 |
|
|
13:55 — 17:19
|
13:55 — 17:19
UA580
United Airlines
Chicago — Boston
|
2h 24m |
Find flight
from$200 |
|
|
14:28 — 18:06
|
14:28 — 18:06
UA2138
United Airlines
Chicago — Boston
|
2h 38m |
Find flight
from$239 |
|
|
16:20 — 19:48
|
16:20 — 19:48
UA1677
United Airlines
Chicago — Boston
|
2h 28m |
Find flight
from$167 |
|
|
18:25 — 21:57
|
18:25 — 21:57
UA1989
United Airlines
Chicago — Boston
|
2h 32m |
Find flight
from$129 |
|
|
19:49 — 23:16
|
19:49 — 23:16
UA1129
United Airlines
Chicago — Boston
|
2h 27m |
Find flight
from$202 |
|
|
21:20 — 00:45
+1 day
|
21:20 — 00:45
UA1237
United Airlines
Chicago — Boston
|
2h 25m |
Find flight
from$285 |
|
|
21:32 — 00:59
+1 day
|
21:32 — 00:59
UA1779
United Airlines
Chicago — Boston
|
2h 27m |
Find flight
from$140 |
|
|
05:05 — 14:44
|
05:05 — 09:06
NK2
Spirit Airlines
Chicago — Miami
2h 23m stop
12:29 — 15:44
NK2126
Spirit Airlines
Miami — Boston
|
8h 39m including layover |
Find flight
from$117 |
|
|
06:00 — 11:10
+1 day
|
06:00 — 09:04
F93352
Frontier Airlines
Chicago — Raleigh
23h 55m stop
08:59 — 11:10
F93058
Frontier Airlines
Raleigh — Boston
|
28h 10m including layover |
Find flight
from$118 |
|
|
06:00 — 18:59
|
06:00 — 08:27
HA6176
Hawaiian Airlines
Chicago — Seattle
1h 59m stop
10:26 — 18:59
HA6629
Hawaiian Airlines
Seattle — Boston
|
11h 59m including layover |
Find flight
from$213 |
|
|
07:47 — 09:09
+1 day
|
07:47 — 11:26
NK2550
Spirit Airlines
Chicago — Orlando
18h 41m stop
06:07 — 09:09
NK2090
Spirit Airlines
Orlando — Boston
|
24h 22m including layover |
Find flight
from$174 |
|
|
08:45 — 15:54
|
08:45 — 12:02
UA782
United Airlines
Chicago — Newark
2h 33m stop
14:35 — 15:54
UA1176
United Airlines
Newark — Boston
|
6h 9m including layover |
Find flight
from$212 |
|
|
09:12 — 12:01
+1 day
|
09:12 — 11:23
G43081
Allegiant Air
Chicago — Fort Walton Beach
20h 37m stop
08:00 — 12:01
G41443
Allegiant Air
Fort Walton Beach — Boston
|
25h 49m including layover |
Find flight
from$124 |
|
|
10:34 — 09:47
+1 day
|
10:34 — 13:11
G4218
Allegiant Air
Chicago — Fletcher
18h 24m stop
07:35 — 09:47
G4232
Allegiant Air
Fletcher — Boston
|
22h 13m including layover |
Find flight
from$114 |
|
|
10:46 — 23:47
|
10:46 — 14:30
NK2189
Spirit Airlines
Chicago — Orlando
6h 12m stop
20:42 — 23:47
NK2258
Spirit Airlines
Orlando — Boston
|
12h 1m including layover |
Find flight
from$179 |
|
|
11:14 — 19:32
|
11:14 — 14:10
UA466
United Airlines
Chicago — Washington D.C.
3h 40m stop
17:50 — 19:32
UA688
United Airlines
Washington D.C. — Boston
|
7h 18m including layover |
Find flight
from$204 |
|
|
12:41 — 23:29
|
12:41 — 16:44
NK2187
Spirit Airlines
Chicago — Miami
3h 29m stop
20:13 — 23:29
NK2212
Spirit Airlines
Miami — Boston
|
9h 48m including layover |
Find flight
from$129 |
|
|
13:34 — 19:39
|
13:34 — 16:36
NK2521
Spirit Airlines
Chicago — Myrtle Beach
55m stop
17:31 — 19:39
NK2522
Spirit Airlines
Myrtle Beach — Boston
|
5h 5m including layover |
Find flight
from$195 |
|
|
14:53 — 08:17
+1 day
|
14:53 — 17:18
G43025
Allegiant Air
Chicago — Knoxville
12h 42m stop
06:00 — 08:17
G41409
Allegiant Air
Knoxville — Boston
|
16h 24m including layover |
Find flight
from$181 |
|
|
15:40 — 22:26
|
15:40 — 19:08
UA2216
United Airlines
Chicago — Newark
1h 51m stop
20:59 — 22:26
UA1393
United Airlines
Newark — Boston
|
5h 46m including layover |
Find flight
from$134 |
|
|
16:00 — 09:34
+1 day
|
16:00 — 19:43
F91186
Frontier Airlines
Chicago — Tampa
10h 37m stop
06:20 — 09:34
F91216
Frontier Airlines
Tampa — Boston
|
16h 34m including layover |
Find flight
from$118 |
|
|
16:15 — 00:44
+1 day
|
16:15 — 20:18
F93044
Frontier Airlines
Chicago — Orlando
1h 15m stop
21:33 — 00:44
F93348
Frontier Airlines
Orlando — Boston
|
7h 29m including layover |
Find flight
from$102 |
|
|
05:05 — 09:35
+1 day
|
05:05 — 09:06
NK2
Spirit Airlines
Chicago — Miami
7h 8m stop
16:14 — 17:40
NK2410
Spirit Airlines
Miami — Nashville
12h 20m stop
06:00 — 09:35
NK2237
Spirit Airlines
Nashville — Boston
|
27h 30m including layover |
Find flight
from$197 |
|
|
07:47 — 13:30
+1 day
|
07:47 — 11:26
NK2550
Spirit Airlines
Chicago — Orlando
6h 29m stop
17:55 — 19:25
NK2088
Spirit Airlines
Orlando — Myrtle Beach
15h 59m stop
11:24 — 13:30
NK2658
Spirit Airlines
Myrtle Beach — Boston
|
28h 43m including layover |
Find flight
from$175 |
|
|
08:17 — 18:58
+1 day
|
08:17 — 12:30
NK2193
Spirit Airlines
Chicago — Miami
17h 30m stop
06:00 — 08:14
NK2045
Spirit Airlines
Miami — Dallas
5h 52m stop
14:06 — 18:58
NK2151
Spirit Airlines
Dallas — Boston
|
33h 41m including layover |
Find flight
from$169 |
|
|
09:55 — 13:30
+1 day
|
09:55 — 14:02
NK2187
Spirit Airlines
Chicago — Miami
5h 18m stop
19:20 — 21:05
NK2657
Spirit Airlines
Miami — Myrtle Beach
14h 19m stop
11:24 — 13:30
NK2658
Spirit Airlines
Myrtle Beach — Boston
|
26h 35m including layover |
Find flight
from$175 |
|
|
11:50 — 09:09
+1 day
|
11:50 — 13:51
NK2620
Spirit Airlines
Chicago — Las Vegas
8h 3m stop
21:54 — 05:25
NK2297
Spirit Airlines
Las Vegas — Orlando
42m stop
06:07 — 09:09
NK2090
Spirit Airlines
Orlando — Boston
|
20h 19m including layover |
Find flight
from$191 |
|
|
13:59 — 08:41
+1 day
|
13:59 — 16:57
NK2521
Spirit Airlines
Chicago — Myrtle Beach
1h 5m stop
18:02 — 20:01
NK2475
Spirit Airlines
Myrtle Beach — Detroit
10h 44m stop
06:45 — 08:41
NK2149
Spirit Airlines
Detroit — Boston
|
17h 42m including layover |
Find flight
from$169 |
|
|
17:50 — 19:09
+1 day
|
17:50 — 19:19
NK2029
Spirit Airlines
Chicago — Nashville
9h 51m stop
05:10 — 07:49
NK2243
Spirit Airlines
Nashville — Detroit
9h 29m stop
17:18 — 19:09
NK2149
Spirit Airlines
Detroit — Boston
|
24h 19m including layover |
Find flight
from$211 |
|
|
17:50 — 09:03
+1 day
|
17:50 — 19:19
NK2029
Spirit Airlines
Chicago — Nashville
2h 18m stop
21:37 — 00:36
NK2040
Spirit Airlines
Nashville — Orlando
5h 29m stop
06:05 — 09:03
NK2090
Spirit Airlines
Orlando — Boston
|
14h 13m including layover |
Find flight
from$225 |
|
|
21:02 — 09:09
+2 days
|
21:02 — 23:07
NK2179
Spirit Airlines
Chicago — Las Vegas
22h 47m stop
21:54 — 05:25
NK2297
Spirit Airlines
Las Vegas — Orlando
42m stop
06:07 — 09:09
NK2090
Spirit Airlines
Orlando — Boston
|
35h 7m including layover |
Find flight
from$191 |
|
*Departure and arrival times - local. Updated on May 13, 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 27m.
- The fastest flight 2h 24m
- Average flight time 2h 27m
- The earliest flight 05:05
- The latest flight 22:15
- Distance 852 ml
The cheapest months to travel to Boston are january (from 84 $), may (from 102 $), june (from 114 $).
The most expensive months are november (from 254 $), june (from 114 $), may (from 102 $).
What is the lowest airfare Chicago to Boston?
The cheapest plane ticket found by our users is $102. This airfare is for economy class on one-way F93044 flight by Frontier Airlines for May 17, 2025 which leaves O'Hare International in Chicago at 16:15 am and arrives at Boston Logan at 00:44.
Economy class
$102
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 United Airlines - 73 departures per week at the price of from $ 129 . And the most expensive tickets are offered by Finnair airline - from $ 3490.
Direct flights
There are 12 nonstop flights on the route. The fastest direct flight is UA580 by United Airlines takes 2h 24m and the cheapest is F93044 by Frontier Airlines for $129.
- from $129Find
See more direct flights
Connecting Flights
There are 164 flights with layovers on the route. The fastest connecting flight is UA2277 by United Airlines takes 4h 24m and the cheapest is F93044 by Frontier Airlines for $102.
- from $134Find
- from $117Find
- AS - Alaska Airlinesfrom $259Find
- F9 - Frontier Airlinesfrom $102Find
- SY - Sun Country Airlinesfrom $265Find
- AY - Finnairfrom $2293Find
- HA - Hawaiian Airlinesfrom $213Find
- G4 - Allegiant Airfrom $114Find
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 $102Find
- Midway-MDWfrom $114Find
- 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.
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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.
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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.