Cheap Flights from Boston, MA to Chicago, IL from $59
On Cheapflightsplus.com you will find 22 direct and 500 connecting flights from Boston to Chicago. You can compare airfare deals from 8 airlines and multiple travel sites from $59, book and save on cheap plane tickets and last minute offers. Also check out BOS-CHI 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 Boston to Chicago depends on and how to choose the most interesting flight option for you.
Distance between Boston and Chicago is 1370 miles. Time difference between the cities is 1h. Airplanes depart 05:30 to 21:40 from 4 Boston airports and arrive 05:30 to 21:40 to 7 Chicago airports. Average flight time is 2h 51m.
- The fastest flight 2h 47m
- Average flight time 2h 51m
- The earliest flight 05:30
- The latest flight 21:40
- Distance 852 ml
Best Flights from Boston to Chicago Today
| Price | Departure | Arrival | Flight Duration | Airline | Flight |
|---|---|---|---|---|---|
| from $74 | 16:27 Boston Logan | 18:20 Chicago O'Hare International | 2h 53m | United Airlines | UA2040 |
| from $101 | 20:44 Boston Logan | 22:32 Chicago O'Hare International | 2h 48m | United Airlines | UA2229 |
| from $124 | 10:40 Boston Logan | 12:31 Chicago O'Hare International | 2h 51m | United Airlines | UA1298 |
| from $59 | 06:10 Boston Logan | 14:34 Chicago O'Hare International | 9h 24m layover 2h 45m - Miami | Spirit Airlines | NK296 NK866 |
| from $70 | 17:42 Boston Logan | 23:29 Chicago O'Hare International | 6h 47m layover 0h 32m - Orlando | Spirit Airlines | NK2093 NK2190 |
The cheapest months to travel to Chicago are august (from 59 $), october (from 68 $), may (from 70 $).
The most expensive months are january (from 284 $), december (from 118 $), september (from 90 $).
What is the lowest airfare Boston to Chicago?
The cheapest plane ticket found by our users is $59. This airfare is for economy class on one-way NK2887 flight by Spirit Airlines for October 7, 2025 which leaves Logan in Boston at 11:56 am and arrives at Chicago O'Hare International at 20:40.
Flight Schedule Boston (Massachusetts) to Chicago (Illinois)
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Popular Airlines on the Route
The flight Boston — Chicago is served by 8 regular airlines and 4 low-cost airlines. Most of the flights on this route are operated by Alaska Airlines - 27 departures per week at the price of from $ 203 . And the most expensive tickets are offered by SWISS International Air Lines airline - from $ 6035.
Direct flights
There are 22 nonstop flights on the route. The fastest direct flight is UA1989 by United Airlines takes 2h 47m and the cheapest is NK2887 by Spirit Airlines for $74.
- UA - United Airlinesfrom $74Find
Connecting Flights
There are 500 flights with layovers on the route. The fastest connecting flight is NK2106 by Spirit Airlines takes 4h 23m and the cheapest is NK2887 by Spirit Airlines for $59.
- AS - Alaska Airlinesfrom $203Find
- F9 - Frontier Airlinesfrom $94Find
- SY - Sun Country Airlinesfrom $139Find
- HA - Hawaiian Airlinesfrom $216Find
- UA - United Airlinesfrom $114Find
- LX - SWISS International Air Linesfrom $6035Find
- NK - Spirit Airlinesfrom $59Find
- G4 - Allegiant Airfrom $89Find
Airports
You can fly from Boston to Chicago from 4 airports (Boston City Heliport, Boston RT128 Rail, Boston South Rail, Logan).
Boston airports
- Boston City Heliport-JBCFind
- Boston RT128 Rail-ZRUFind
- Boston South Rail-ZTOFind
- Logan-BOSfrom $59Find
Chicago airports
- O'Hare International-ORDFind
- Midway-MDWFind
- Dupage County-DPAFind
- Chicago FSS-CHIFind
- Merrill C Meigs (closed)-CGXFind
- Pal-Waukee-PWKFind
- Chicago NAS-NOHFind
Airplanes
There are flights to Chicago from Boston by 8 airlines that use 0 aircraft brands. They range from huge modern airplanes to small-sized.
Top Domestic Destinations from Boston
You may also consider searching for discounted plane tickets to some other popular places from Boston within United States.
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Top International Destinations from Boston
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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