Cheap Flights from Chicago, IL to Boston, MA from $95
Return flight: Boston – Chicago
On Cheapflightsplus.com you will find 3 direct and 50 connecting flights from Chicago to Boston. You can compare airfare deals from 7 airlines and multiple travel sites from $95, 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: $95 (one-way), $163 (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 $95. The fastest direct flight takes 2h 26m and the fastest connecting – 4h 22m.
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $95 | 19:53 Chicago O'Hare International | 23:20 Boston Logan | 2h 27m | United Airlines | UA2444 |
| from $107 | 06:30 Chicago O'Hare International | 09:56 Boston Logan | 2h 26m | United Airlines | UA2104 |
| from $107 | 07:49 Chicago O'Hare International | 11:16 Boston Logan | 2h 27m | United Airlines | UA2067 |
| from $116 | 16:06 Chicago Midway | 00:43+1 день Boston Logan | 7h 37m layover 1h 35m - Tampa | Frontier Airlines | F91186 F91216 |
| from $137 | 07:10 Chicago O'Hare International | 13:28 Boston Logan | 5h 18m layover 1h 45m - Newark | United Airlines | UA563 UA2265 |
| from $137 | 06:00 Chicago O'Hare International | 13:28 Boston Logan | 6h 28m layover 3h 0m - Newark | United Airlines | UA1658 UA2265 |
| from $172 | 08:52 Chicago O'Hare International | 14:14 Boston Logan | 4h 22m layover 0h 40m - Washington D.C. | United Airlines | UA2029 UA2710 |
| from $177 | 05:05 Chicago O'Hare International | 15:37 Boston Logan | 9h 32m layover 3h 10m - Miami | Spirit Airlines | NK1 NK2126 |
| from $180 | 07:56 Chicago O'Hare International | 09:03+1 день Boston Logan | 24h 7m layover 18h 25m - Orlando | Spirit Airlines | NK2550 NK2090 |
| from $221 | 07:56 Chicago O'Hare International | 23:47 Boston Logan | 14h 51m layover 9h 2m - Orlando | Spirit Airlines | NK2550 NK2258 |
| from $257 | 21:31 Chicago O'Hare International | 17:41+1 день Boston Logan | 19h 10m layover 15h 30m - Washington D.C. | United Airlines | UA276 UA1856 |
| from $264 | 21:24 Chicago O'Hare International | 10:23+1 день Boston Logan | 11h 59m layover 8h 17m - Newark | United Airlines | UA396 UA375 |
| from $135 | 21:28 Chicago O'Hare International | 23:47+1 день Boston Logan | 25h 19m layover 11h 9m - New York 5h 55m - Orlando | Spirit Airlines | NK2542 NK2392 NK2258 |
| from $165 | 10:19 Chicago O'Hare International | 23:47 Boston Logan | 12h 28m layover 3h 51m - Baltimore 1h 5m - Orlando | Spirit Airlines | NK2440 NK1961 NK2258 |
| from $188 | 11:45 Chicago O'Hare International | 18:51+1 день Boston Logan | 30h 6m layover 0h 30m - Fort Leonard Wood 22h 26m - Dallas | flynordic | LF3539 LF3551 NK2151 |
| from $207 | 10:43 Chicago O'Hare International | 23:47 Boston Logan | 12h 4m layover 1h 5m - Atlanta 4h 29m - Orlando | Spirit Airlines | NK2708 NK2460 NK2258 |
Show all tickets
*Departure and arrival times - local. Prices indicated for one-way flights. Information updated on July 23, 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$107 |
|
|
07:49 — 11:16
|
07:49 — 11:16
UA2067
United Airlines
Chicago — Boston
|
2h 27m |
Find flight
from$107 |
|
|
19:53 — 23:20
|
19:53 — 23:20
UA2444
United Airlines
Chicago — Boston
|
2h 27m |
Find flight
from$95 |
|
|
05:05 — 15:37
|
05:05 — 09:12
NK1
Spirit Airlines
Chicago — Miami
3h 10m stop
12:22 — 15:37
NK2126
Spirit Airlines
Miami — Boston
|
9h 32m including layover |
Find flight
from$177 |
|
|
06:00 — 13:28
|
06:00 — 09:13
UA1658
United Airlines
Chicago — Newark
3h stop
12:13 — 13:28
UA2265
United Airlines
Newark — Boston
|
6h 28m including layover |
Find flight
from$137 |
|
|
07:10 — 13:28
|
07:10 — 10:28
UA563
United Airlines
Chicago — Newark
1h 45m stop
12:13 — 13:28
UA2265
United Airlines
Newark — Boston
|
5h 18m including layover |
Find flight
from$137 |
|
|
08:00 — 23:59
|
08:00 — 10:39
AS683
Alaska Airlines
Chicago — Seattle
5h 4m stop
15:43 — 23:59
AS460
Alaska Airlines
Seattle — Boston
|
14h 59m including layover |
Find flight
from$783 |
|
|
08:52 — 14:14
|
08:52 — 11:55
UA2029
United Airlines
Chicago — Washington D.C.
40m stop
12:35 — 14:14
UA2710
United Airlines
Washington D.C. — Boston
|
4h 22m including layover |
Find flight
from$172 |
|
|
09:55 — 22:56
|
09:55 — 14:06
NK3187
Spirit Airlines
Chicago — Miami
5h 32m stop
19:38 — 22:56
NK2212
Spirit Airlines
Miami — Boston
|
12h 1m including layover |
Find flight
from$309 |
|
|
14:33 — 23:53
|
14:33 — 16:26
UA503
United Airlines
Chicago — Denver
1h 24m stop
17:50 — 23:53
UA1218
United Airlines
Denver — Boston
|
8h 20m including layover |
Find flight
from$716 |
|
|
16:06 — 00:43
+1 day
|
16:00 — 19:43
F91186
Frontier Airlines
Chicago — Tampa
1h 35m stop
06:20 — 09:34
F91216
Frontier Airlines
Tampa — Boston
|
7h 37m including layover |
Find flight
from$116 |
|
|
16:20 — 06:01
+1 day
|
15:45 — 17:39
UA1801
United Airlines
Chicago — Denver
5h 47m stop
23:40 — 05:39
UA2610
United Airlines
Denver — Boston
|
12h 41m including layover |
Find flight
from$337 |
|
|
17:54 — 08:00
+1 day
|
17:54 — 20:34
HA6296
Hawaiian Airlines
Chicago — Seattle
3h 6m stop
23:40 — 08:00
HA6628
Hawaiian Airlines
Seattle — Boston
|
13h 6m including layover |
Find flight
from$295 |
|
|
17:57 — 10:23
+1 day
|
17:57 — 21:30
UA534
United Airlines
Chicago — Newark
11h 35m stop
09:05 — 10:23
UA375
United Airlines
Newark — Boston
|
15h 26m including layover |
Find flight
from$643 |
|
|
20:08 — 12:02
+1 day
|
20:08 — 21:58
UA2040
United Airlines
Chicago — Denver
8h 2m stop
06:00 — 12:02
UA2454
United Airlines
Denver — Boston
|
14h 54m including layover |
Find flight
from$691 |
|
|
05:15 — 14:31
|
05:15 — 08:58
NK2189
Spirit Airlines
Chicago — Orlando
1h 9m stop
10:07 — 11:31
NK2645
Spirit Airlines
Orlando — Myrtle Beach
55m stop
12:26 — 14:31
NK2658
Spirit Airlines
Myrtle Beach — Boston
|
8h 16m including layover |
Find flight
from$275 |
|
|
10:19 — 23:47
|
10:19 — 13:13
NK2440
Spirit Airlines
Chicago — Baltimore
3h 51m stop
17:04 — 19:37
NK1961
Spirit Airlines
Baltimore — Orlando
1h 5m stop
20:42 — 23:47
NK2258
Spirit Airlines
Orlando — Boston
|
12h 28m including layover |
Find flight
from$165 |
|
|
10:43 — 23:47
|
10:31 — 13:30
NK2708
Spirit Airlines
Chicago — Atlanta
1h 5m stop
16:30 — 17:58
NK2460
Spirit Airlines
Atlanta — Orlando
4h 29m stop
20:42 — 23:47
NK2258
Spirit Airlines
Orlando — Boston
|
12h 4m including layover |
Find flight
from$207 |
|
|
11:45 — 18:51
+1 day
|
11:45 — 13:25
LF3539
flynordic
Chicago — Fort Leonard Wood
30m stop
13:55 — 15:40
LF3551
flynordic
Fort Leonard Wood — Dallas
22h 26m stop
14:06 — 18:51
NK2151
Spirit Airlines
Dallas — Boston
|
30h 6m including layover |
Find flight
from$188 |
|
|
13:43 — 07:12
+1 day
|
08:17 — 12:30
NK2193
Spirit Airlines
Chicago — Miami
2h 45m stop
20:52 — 23:33
NK2426
Spirit Airlines
Miami — Baltimore
6h 18m stop
05:35 — 07:03
NK2516
Spirit Airlines
Baltimore — Boston
|
16h 29m including layover |
Find flight
from$266 |
|
|
14:25 — 13:28
+1 day
|
14:25 — 16:53
UA2329
United Airlines
Chicago — Detroit
16h 17m stop
09:10 — 11:00
UA3403
United Airlines
Detroit — Newark
1h 13m stop
12:13 — 13:28
UA2265
United Airlines
Newark — Boston
|
22h 3m including layover |
Find flight
from$642 |
|
|
18:05 — 14:14
+1 day
|
18:05 — 20:39
UA5833
United Airlines
Chicago — Detroit
13h 31m stop
10:10 — 11:46
UA3441
United Airlines
Detroit — Washington D.C.
49m stop
12:35 — 14:14
UA2710
United Airlines
Washington D.C. — Boston
|
19h 9m including layover |
Find flight
from$642 |
|
|
19:35 — 14:14
+1 day
|
19:35 — 22:08
UA5785
United Airlines
Chicago — Detroit
12h 2m stop
10:10 — 11:46
UA3441
United Airlines
Detroit — Washington D.C.
49m stop
12:35 — 14:14
UA2710
United Airlines
Washington D.C. — Boston
|
17h 39m including layover |
Find flight
from$642 |
|
|
21:28 — 23:47
+1 day
|
21:08 — 00:29
NK2542
Spirit Airlines
Chicago — New York
11h 9m stop
11:55 — 14:40
NK2392
Spirit Airlines
New York — Orlando
5h 55m stop
20:42 — 23:47
NK2258
Spirit Airlines
Orlando — Boston
|
25h 19m including layover |
Find flight
from$135 |
|
|
21:28 — 16:41
+1 day
|
21:28 — 00:46
NK2542
Spirit Airlines
Chicago — Newark
4h 39m stop
06:59 — 09:24
NK2217
Spirit Airlines
Newark — Atlanta
6h 16m stop
14:07 — 16:41
NK2092
Spirit Airlines
Atlanta — Boston
|
18h 13m including layover |
Find flight
from$252 |
|
*Departure and arrival times - local. Updated on July 23, 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 05:02 to 21:45 from 7 Chicago airports and arrive 05:02 to 21:45 to 4 Boston airports. Average flight time is 2h 27m.
- The fastest flight 2h 26m
- Average flight time 2h 27m
- The earliest flight 05:02
- The latest flight 21:45
- Distance 852 ml
The cheapest months to travel to Boston are may (from 95 $), july (from 106 $), june (from 107 $).
The most expensive months are november (from 4 250 $), september (from 110 $), october (from 110 $).
What is the lowest airfare Chicago to Boston?
The cheapest plane ticket found by our users is $95. This airfare is for economy class on one-way UA2444 flight by United Airlines for June 15, 2025 which leaves O'Hare International in Chicago at 19:53 am and arrives at Boston Logan at 23:20.
Economy class
$95
Business class
?
First class
?
Popular Airlines on the Route
The flight Chicago — Boston is served by 7 regular airlines and 2 low-cost airlines. Most of the flights on this route are operated by United Airlines - 30 departures per week at the price of from $ 95 . And the most expensive tickets are offered by Finnair airline - from $ 2099.
Direct flights
There are 3 nonstop flights on the route. The fastest direct flight is UA2104 by United Airlines takes 2h 26m and the cheapest is UA2444 by United Airlines for $95.
- from $95Find
See more direct flights
Connecting Flights
There are 50 flights with layovers on the route. The fastest connecting flight is UA2029 by United Airlines takes 4h 22m and the cheapest is UA2444 by United Airlines for $116.
- from $137Find
- from $135Find
- AS - Alaska Airlinesfrom $426Find
- F9 - Frontier Airlinesfrom $116Find
- AY - Finnairfrom $2099Find
- HA - Hawaiian Airlinesfrom $288Find
- LF - flynordicfrom $188Find
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 $95Find
- Midway-MDWfrom $116Find
- 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 7 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.