Prices shown are for 1 adult ticket including taxes & fees.(As ticket fares can change frequently, these advertised prices are for reference only. The actual prices will be shown at time of booking.)
Airlines adjust prices for plane tickets based on the day and time that you book your flight. After analyzing data from all airlines, we have discovered that the best days to book flights from Boston to Chicago are Tuesdays, Wednesdays, and Saturdays.
Airlines flying from Boston to Chicago include American Airlines,Japan Airlines,Jetblue Airways,United Airlines,Spirit Airlines.
United Airlines provides 327 of the non-stop flights between Boston and Chicago.
There are 5 airports in Chicago - O'Hare International Airport,Midway International Airport,Chicago Du Page County Apt,Chicago Palwaukee Apt,Rockford International Airport.
2h56m
BOS ✈ CHI
From US$37
| Flight info. | Departure | Arrival | Route | Weekly Schedule | |
|---|---|---|---|---|---|
AA1221 American Airlines | 05:00 BOS 07:05 ORD | Boston to Chicago | ---W-F- | Search | |
AA2265 American Airlines | 06:00 BOS 07:41 ORD | Boston to Chicago | S------ | Search | |
B6111 Jetblue Airways | 06:28 BOS 08:23 ORD | Boston to Chicago | ------S | Search | |
AS4231 Alaska Airlines | 06:54 BOS 08:54 ORD | Boston to Chicago | ---W--- | Search | |
UA449 United Airlines | 07:00 BOS 09:00 ORD | Boston to Chicago | SMT-TFS | Search | |
AA2262 American Airlines | 07:41 BOS 09:44 ORD | Boston to Chicago | S------ | Search | |
JL7313 Japan Airlines | 09:00 BOS 11:00 ORD | Boston to Chicago | -M----- | Search | |
AA242 American Airlines | 09:01 BOS 10:59 ORD | Boston to Chicago | SMTWTF- | Search | |
UA1251 United Airlines | 10:00 BOS 12:00 ORD | Boston to Chicago | SMTWTFS | Search | |
AA2426 American Airlines | 10:30 BOS 12:27 ORD | Boston to Chicago | ------S | Search | |
AA140 American Airlines | 10:35 BOS 12:16 ORD | Boston to Chicago | S------ | Search | |
AA1287 American Airlines | 12:00 BOS 13:41 ORD | Boston to Chicago | ---WTFS | Search | |
AA1769 American Airlines | 12:01 BOS 14:01 ORD | Boston to Chicago | ------- | Search | |
UA1564 United Airlines | 12:51 BOS 14:49 ORD | Boston to Chicago | SMTWTFS | Search | |
NK773 Spirit Airlines | 13:25 BOS 15:20 ORD | Boston to Chicago | SMTWTFS | Search | |
AA2723 American Airlines | 13:30 BOS 15:28 ORD | Boston to Chicago | SMTWTFS | Search | |
AA2264 American Airlines | 13:35 BOS 15:16 ORD | Boston to Chicago | SM-WT-S | Search | |
AA330 American Airlines | 13:45 BOS 15:44 ORD | Boston to Chicago | ------- | Search | |
AA1166 American Airlines | 15:00 BOS 17:03 ORD | Boston to Chicago | ------- | Search | |
AA111 American Airlines | 17:00 BOS 19:18 ORD | Boston to Chicago | SMTWTFS | Search | |
AA239 American Airlines | 17:04 BOS 19:20 ORD | Boston to Chicago | SMTWTFS | Search | |
AA2091 American Airlines | 17:15 BOS 19:18 ORD | Boston to Chicago | ------- | Search | |
AA834 American Airlines | 17:28 BOS 19:35 ORD | Boston to Chicago | SMTWTFS | Search | |
UA439 United Airlines | 18:15 BOS 20:13 ORD | Boston to Chicago | ------S | Search | |
AD7019 Azul | 18:22 BOS 20:22 ORD | Boston to Chicago | ------S | Search | |
AA868 American Airlines | 18:35 BOS 20:16 ORD | Boston to Chicago | ------- | Search | |
AA131 American Airlines | 19:10 BOS 21:09 ORD | Boston to Chicago | SMTWTFS | Search | |
AA1109 American Airlines | 19:14 BOS 21:25 ORD | Boston to Chicago | SMT-TFS | Search | |
AA2084 American Airlines | 19:15 BOS 21:23 ORD | Boston to Chicago | ------- | Search | |
AA2321 American Airlines | 19:22 BOS 21:30 ORD | Boston to Chicago | ------- | Search | |
There is usually no major price difference between buying a roundtrip flight versus a one-way flight. Increased flexibility is the main benefit when it comes to buying a one-way flight from Boston(BOS) to Chicago(CHI). However, booking a roundtrip flight is a simpler process. You can compare roundtrip and one-way flights by using our flight comparison tool.
Chicago attracts thousands of visitors every year for both business and pleasure. Planning a trip from Boston to Chicago is easy when you use Trip.com to help you make travel arrangements. With Trip.com, you can search for available flights and hotel rooms, and then make your booking quickly and easily online.
Make your journey from Boston (BOS) to Chicago (CHI) a trip to remember when you use Trip.com to review city attractions before you arrive. With a preview of what's available at your destination, you can make any necessary reservations in advance for the best travel experience possible.
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