Cheap flights from Boston, MA
to Chicago, IL
Flights starting at $90. Choose between Delta Air Lines, American Airlines, or Frontier Airlines to find the best price.
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Cheapest one-way trip | $96 |
|---|---|
Cheapest round-trip | $185 |
Average round-trip | $245 |
Nonstop flights in June | $98 – $1096 |
Most popular airline | Delta Air Lines |
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Weekly direct flights
Discover the top airlines offering direct flights from Boston to Chicago in the next month. You’ll find the number of daily direct flights per airline in the table.
Weekly direct flights for Sun 28.05 - Sat 03.06
| Airline | Sun 28.05 | Mon 29.05 | Tue 30.05 | Wed 31.05 | Thu 01.06 | Fri 02.06 | Sat 03.06 |
|---|---|---|---|---|---|---|---|
| 6 | 1 | 3 | 5 | 1 | --- | 5 | |
| 4 | 3 | 3 | 5 | 1 | --- | 1 | |
| 3 | 2 | 5 | 3 | --- | --- | 2 | |
| 1 | 1 | 1 | 1 | --- | --- | 1 |
Weekly direct flights for Sun 04.06 - Sat 10.06
| Airline | Sun 04.06 | Mon 05.06 | Tue 06.06 | Wed 07.06 | Thu 08.06 | Fri 09.06 | Sat 10.06 |
|---|---|---|---|---|---|---|---|
| 1 | 5 | 7 | 5 | 2 | 2 | 5 | |
| 1 | 1 | 3 | 4 | 1 | --- | --- | |
| --- | 2 | 1 | 1 | --- | --- | --- | |
| --- | 1 | 1 | 1 | --- | --- | --- |
Weekly direct flights for Sun 11.06 - Sat 17.06
| Airline | Sun 11.06 | Mon 12.06 | Tue 13.06 | Wed 14.06 | Thu 15.06 | Fri 16.06 | Sat 17.06 |
|---|---|---|---|---|---|---|---|
| 2 | 5 | 7 | 5 | 5 | 2 | 6 | |
| 2 | 4 | 4 | 4 | 3 | 2 | 2 | |
| --- | 3 | 5 | 4 | 4 | 1 | 2 | |
| --- | 1 | 1 | 1 | 3 | --- | 1 |
Weekly direct flights for Sun 18.06 - Sat 24.06
| Airline | Sun 18.06 | Mon 19.06 | Tue 20.06 | Wed 21.06 | Thu 22.06 | Fri 23.06 | Sat 24.06 |
|---|---|---|---|---|---|---|---|
| 2 | 3 | 7 | 4 | 1 | 2 | 4 | |
| 2 | 2 | 5 | 5 | 2 | 1 | --- | |
| 1 | 2 | 4 | 4 | 3 | 1 | --- | |
| --- | 1 | 1 | 1 | 1 | --- | 1 |
Check-in for a flight from Boston to Chicago
| Name | Carrier code | IATA Code | Passport needed during booking | Online check-in available |
|---|---|---|---|---|
| Delta Air Lines | DAL | DL | Yes | Opens 24 days before flight Closes 1 hours before flight |
| American Airlines | AAL | AA | Yes | No |
| Frontier Airlines | FFT | F9 | No | Opens 24 days before flight Closes 1 hours before flight |
| United Airlines | UAL | UA | Yes | No |
| JetBlue Airways | JBU | B6 | No | Opens 24 days before flight Closes 2 hours before flight |
United States COVID-19 travel restrictions
Most travelers from Boston, BOS can enter Chicago, ORD.
Departure
| Travel restrictions |
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Return
| Travel restrictions |
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Information is provided as guidance only and accurate at the time of publishing. Always check government websites and airline materials before booking and traveling.
Learn more about COVID-19 restrictions in United States in our dedicated Stories article.
Frequently asked questions
Planning a trip? Thanks to our Virtual Interlining algorithm, we offer billions of route combinations between any A and any B in the world by plane, train, and bus. Find the cheapest routes and best deals for you, as well as the best dates on which to travel.
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