Cheap Flights from Chicago, IL to Boston, MA from $59
Return flight: Boston – Chicago
On Cheapflightsplus.com you will find 6 direct and 86 connecting flights from Chicago to Boston. You can compare airfare deals from 6 airlines and multiple travel sites from $59, 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: $59 (one-way), $101 (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 $59. The fastest direct flight takes 2h 19m and the fastest connecting – 4h 21m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $115 | 18:35 Chicago O'Hare International | 21:59 Boston Logan | 2h 24m | United Airlines | UA1989 |
| from $115 | 07:30 Chicago O'Hare International | 10:56 Boston Logan | 2h 26m | United Airlines | UA1083 |
| from $115 | 09:20 Chicago O'Hare International | 12:46 Boston Logan | 2h 26m | United Airlines | UA691 |
| from $229 | 07:30 Chicago O'Hare International | 10:49 Boston Logan | 2h 19m | United Airlines | UA414 |
| from $59 | 14:28 Chicago O'Hare International | 23:32 Boston Logan | 8h 4m layover 1h 37m - Miami | Spirit Airlines | NK717 NK866 |
| from $59 | 12:00 Chicago O'Hare International | 21:54 Boston Logan | 8h 54m layover 3h 3m - Orlando | Spirit Airlines | NK1686 NK2989 |
| from $59 | 08:00 Chicago O'Hare International | 18:25 Boston Logan | 9h 25m layover 3h 32m - Orlando | Spirit Airlines | NK1686 NK794 |
| from $82 | 08:13 Chicago O'Hare International | 18:25 Boston Logan | 9h 12m layover 3h 19m - Orlando | Spirit Airlines | NK222 NK794 |
| from $86 | 05:01 Chicago O'Hare International | 11:46 Boston Logan | 5h 45m layover 2h 17m - Philadelphia | Frontier Airlines | F92112 F93012 |
| from $124 | 11:51 Chicago O'Hare International | 17:12 Boston Logan | 4h 21m layover 0h 51m - Newark | United Airlines | UA2133 UA1835 |
| from $124 | 15:15 Chicago O'Hare International | 20:46 Boston Logan | 4h 31m layover 0h 59m - Newark | United Airlines | UA2649 UA1393 |
| from $124 | 12:51 Chicago O'Hare International | 18:26 Boston Logan | 4h 35m layover 1h 3m - Newark | United Airlines | UA2238 UA2612 |
| from $124 | 08:50 Chicago O'Hare International | 14:30 Boston Logan | 4h 40m layover 1h 7m - Washington D.C. | United Airlines | UA2490 UA2060 |
| from $124 | 13:15 Chicago O'Hare International | 19:00 Boston Logan | 4h 45m layover 1h 12m - Washington D.C. | United Airlines | UA2431 UA688 |
| from $86 | 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 $103 | 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 January 21, 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 |
|---|---|---|---|---|
|
07:30 — 10:56
|
07:30 — 10:56
UA1083
United Airlines
Chicago — Boston
|
2h 26m |
Find flight
from$115 |
|
|
07:30 — 10:49
|
07:30 — 10:49
UA414
United Airlines
Chicago — Boston
|
2h 19m |
Find flight
from$229 |
|
|
09:15 — 12:38
|
09:15 — 12:38
UA307
United Airlines
Chicago — Boston
|
2h 23m |
Find flight
from$229 |
|
|
09:20 — 12:46
|
09:20 — 12:46
UA691
United Airlines
Chicago — Boston
|
2h 26m |
Find flight
from$115 |
|
|
16:00 — 19:19
|
16:00 — 19:19
UA2475
United Airlines
Chicago — Boston
|
2h 19m |
Find flight
from$229 |
|
|
18:35 — 21:59
|
18:35 — 21:59
UA1989
United Airlines
Chicago — Boston
|
2h 24m |
Find flight
from$115 |
|
|
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$86 |
|
|
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$124 |
|
|
06:00 — 14:07
|
06:00 — 09:11
UA2343
United Airlines
Chicago — Newark
3h 44m stop
12:55 — 14:07
UA1598
United Airlines
Newark — Boston
|
7h 7m including layover |
Find flight
from$124 |
|
|
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$59 |
|
|
08:13 — 18:25
|
08:13 — 12:03
NK222
Spirit Airlines
Chicago — Orlando
3h 19m stop
15:22 — 18:25
NK794
Spirit Airlines
Orlando — Boston
|
9h 12m including layover |
Find flight
from$82 |
|
|
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$124 |
|
|
10:50 — 17:12
|
10:50 — 14:06
UA2091
United Airlines
Chicago — Newark
1h 54m stop
16:00 — 17:12
UA1835
United Airlines
Newark — Boston
|
5h 22m including layover |
Find flight
from$124 |
|
|
10:50 — 18:26
|
10:51 — 14:09
UA2091
United Airlines
Chicago — Newark
3h 4m stop
17:15 — 18:30
UA2612
United Airlines
Newark — Boston
|
6h 36m including layover |
Find flight
from$124 |
|
|
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$124 |
|
|
11:51 — 20:46
|
11:51 — 15:06
UA2133
United Airlines
Chicago — Newark
4h 21m stop
20:20 — 21:35
UA1393
United Airlines
Newark — Boston
|
7h 55m including layover |
Find flight
from$199 |
|
|
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$59 |
|
|
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$124 |
|
|
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$124 |
|
|
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$124 |
|
|
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$59 |
|
|
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$124 |
|
|
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$124 |
|
|
16:08 — 21:36
|
16:08 — 19:23
UA795
United Airlines
Chicago — Newark
57m stop
20:20 — 21:36
UA1393
United Airlines
Newark — Boston
|
4h 28m including layover |
Find flight
from$126 |
|
|
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$124 |
|
|
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$129 |
|
|
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$129 |
|
|
21:45 — 08:13
+1 day
|
21:45 — 00:58
UA2415
United Airlines
Chicago — Newark
6h 2m stop
07:00 — 08:13
UA1420
United Airlines
Newark — Boston
|
9h 28m including layover |
Find flight
from$199 |
|
|
21:45 — 09:16
+1 day
|
21:45 — 00:58
UA2415
United Airlines
Chicago — Newark
7h 2m stop
08:00 — 09:16
UA1109
United Airlines
Newark — Boston
|
10h 31m including layover |
Find flight
from$199 |
|
|
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$103 |
|
|
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$86 |
|
|
07:00 — 21:54
|
07:00 — 10:04
NK1680
Spirit Airlines
Chicago — New York
2h 55m stop
12:59 — 16:04
NK1697
Spirit Airlines
New York — Orlando
2h 46m stop
18:50 — 21:54
NK2989
Spirit Airlines
Orlando — Boston
|
13h 54m including layover |
Find flight
from$115 |
|
*Departure and arrival times - local. Updated on January 21, 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 05:01 to 21:45 from 7 Chicago airports and arrive 05:01 to 21:45 to 4 Boston airports. Average flight time is 2h 24m.
- The fastest flight 2h 19m
- Average flight time 2h 24m
- The earliest flight 05:01
- The latest flight 21:45
- Distance 852 ml
The cheapest months to travel to Boston are january (from 59 $), february (from 82 $), november (from 105 $).
The most expensive months are december (from 128 $), november (from 105 $), february (from 82 $).
What is the lowest airfare Chicago to Boston?
The cheapest plane ticket found by our users is $59. 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
$59
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Boston is served by 6 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 5 departures per week at the price of from $ 207 . And the most expensive tickets are offered by SWISS International Air Lines airline - from $ 5656.
Direct flights
There are 6 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 $115.
- from $115Find
See more direct flights
Connecting Flights
There are 86 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 $59.
- from $207Find
- from $86Find
- from $124Find
- from $59Find
- TK - Turkish Airlinesfrom $1073Find
- LX - SWISS International Air Linesfrom $5656Find
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 $59Find
- Midway-MDWfrom $129Find
- 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.