Cheap Flights from Chicago, IL to Boston, MA from $90
On Cheapflightsplus.com you will find 8 direct and 63 connecting flights from Chicago to Boston. You can compare airfare deals from 6 airlines and multiple travel sites from $90, 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.
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 23:45 from 7 Chicago airports and arrive 05:05 to 23:45 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 23:45
- Distance 852 ml
Best Flights from Chicago to Boston Today
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $90 | 06:30 Chicago O'Hare International | 09:56 Boston Logan | 2h 26m | United Airlines | UA2104 |
| from $131 | 17:57 Chicago O'Hare International | 21:28 Boston Logan | 2h 31m | United Airlines | UA1531 |
| from $159 | 13:12 Chicago O'Hare International | 16:43 Boston Logan | 2h 31m | United Airlines | UA2022 |
| from $134 | 17:55 Chicago O'Hare International | 23:57 Boston Logan | 5h 2m layover 1h 23m - Washington D.C. | United Airlines | UA2677 UA755 |
| from $212 | 10:35 Chicago O'Hare International | 16:28 Boston Logan | 4h 53m layover 1h 18m - Newark | United Airlines | UA1126 UA2033 |
The cheapest months to travel to Boston are october (from 90 $), may (from 90 $), july (from 101 $).
The most expensive months are november (from 4 022 $), september (from 104 $), june (from 102 $).
What is the lowest airfare Chicago to Boston?
The cheapest plane ticket found by our users is $90. This airfare is for economy class on one-way UA2104 flight by United Airlines for October 9, 2025 which leaves O'Hare International in Chicago at 06:30 am and arrives at Boston Logan at 09:56.
Flight Schedule Chicago (Illinois) to Boston (Massachusetts)
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Popular Airlines on the Route
The flight Chicago — Boston is served by 6 regular airlines and 3 low-cost airlines. Most of the flights on this route are operated by Frontier Airlines - 8 departures per week at the price of from $ 349 . And the most expensive tickets are offered by Turkish Airlines airline - from $ 4475.
Direct flights
There are 8 nonstop flights on the route. The fastest direct flight is UA2104 by United Airlines takes 2h 26m and the cheapest is UA2104 by United Airlines for $90.
- UA - United Airlinesfrom $90Find
Connecting Flights
There are 63 flights with layovers on the route. The fastest connecting flight is UA2029 by United Airlines takes 4h 23m and the cheapest is UA2104 by United Airlines for $134.
- F9 - Frontier Airlinesfrom $349Find
- TK - Turkish Airlinesfrom $4475Find
- AY - Finnairfrom $1885Find
- UA - United Airlinesfrom $134Find
- NK - Spirit Airlinesfrom $242Find
- G4 - Allegiant Airfrom $282Find
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 $90Find
- Midway-MDWfrom $282Find
- 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
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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.
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