Cheap Flights from Chicago to Boston (CHI - BOS)
Find deals on over 400 airlines worldwide.
Compare hundreds of travel sites at once.
Save on your next flight to Boston.
CHI BOS Flight Deals
| Sun | Mon | Tue | Wed | Thu | Fri | Sat |
|---|---|---|---|---|---|---|
| 1 $138 | ||||||
| 2 $188 | 3 $173 | 4 $148 | 5 $158 | 6 $178 | 7 $178 | 8 $148 |
| 9 $196 | 10 $158 | 11 $158 | 12 $163 | 13 $168 | 14 $158 | 15 $158 |
| 16 $183 | 17 $173 | 18 $148 | 19 $148 | 20 $190 | 21 $193 | 22 $178 |
| 23 $199 | 24 $193 | 25 $199 | 26 $168 | 27 $193 | 28 $212 | 29 $198 |
| 30 $222 |
Best fares found by users in the last 48 hours.
Related Flights
Return Flight:
From $108 Boston (BOS) - Chicago (CHI)Nearby Airports:
From $108 Chicago (ORD) - Boston (BOS) From $212 Chicago (MDW) - Boston (BOS) From $434 South Bend (SBN) - Boston (BOS) From $202 Chicago (CHI) - Providence (PVD) From $182 Chicago (CHI) - Manchester (MHT) From $408 Chicago (CHI) - Hyannis (HYA)
KAYAK searches hundreds of sites to find the best rate for your next flight from Chicago to Boston. Get the best flight deal for your Boston trip!
Here's how it works. Search KAYAK for a flight ticket from Chicago to Boston. Sort, filter and compare results on one web page.
Then book your plane ticket direct on the airline or travel agent site of your choice!
Direct Flights from Chicago to Boston
Use KAYAK to more easily find direct flights from Chicago (CHI) to Boston (BOS). Select an airline from the list below to see a weekly schedule of direct flights for that airline.
For a more comprehensive list of direct flight information, visit our direct flights tool.
Direct flights CHI - BOS on American Airlines | Flight # | Depart ORD | Arrive BOS | Sun | Mon | Tue | Wed | Thu | Fri | Sat | Valid Between |
|---|---|---|---|---|---|---|---|---|---|---|
| 876 | 6:20 am | 9:30 am | • | • | • | • | • | • | • | May 16 - May 25 |
| 876 | 6:20 am | 9:30 am | • | • | • | • | • | • | • | May 27 - Jun 11 |
| 1640 | 7:55 am | 11:05 am | • | • | • | • | • | May 16 - Jun 11 | ||
| 186 | 10:10 am | 1:20 pm | • | • | • | May 16 - Jun 1 | ||||
| 186 | 10:10 am | 1:20 pm | • | • | • | • | May 17 - May 31 | |||
| 2054 | 1:05 pm | 4:25 pm | • | • | • | • | May 16 - Jun 1 | |||
| 2054 | 1:05 pm | 4:25 pm | • | • | May 17 - May 31 | |||||
| 1096 | 1:35 pm | 4:55 pm | • | May 26 - May 26 | ||||||
| 1096 | 1:35 pm | 4:55 pm | • | May 19 - May 19 | ||||||
| 1618 | 2:25 pm | 5:40 pm | • | • | • | • | • | • | • | May 16 - Jun 11 |
| 2098 | 3:30 pm | 6:50 pm | • | May 26 - May 26 | ||||||
| 2098 | 3:30 pm | 6:50 pm | • | May 18 - Jun 8 | ||||||
| 2098 | 3:30 pm | 6:50 pm | • | • | • | • | • | • | May 27 - Jun 11 | |
| 2098 | 3:30 pm | 6:50 pm | • | • | • | • | • | • | May 16 - May 24 | |
| 5663 | 3:50 pm | 7:05 pm | • | May 30 - May 30 | ||||||
| 1222 | 6:00 pm | 9:20 pm | • | May 16 - May 23 | ||||||
| 1222 | 6:00 pm | 9:20 pm | • | • | • | • | May 17 - Jun 10 | |||
| 1222 | 6:00 pm | 9:20 pm | • | • | May 18 - May 28 | |||||
| 1222 | 6:00 pm | 9:20 pm | • | • | May 30 - Jun 8 | |||||
| 288 | 6:55 pm | 10:15 pm | • | • | • | • | • | • | May 16 - Jun 10 | |
| 1296 | 8:20 pm | 11:35 pm | • | May 21 - May 28 | ||||||
| 1296 | 8:20 pm | 11:35 pm | • | • | • | • | May 17 - May 31 | |||
| 1296 | 8:20 pm | 11:35 pm | • | May 18 - Jun 1 | ||||||
| 1296 | 8:20 pm | 11:35 pm | • | May 16 - May 23 | ||||||
| 1296 | 8:20 pm | 11:35 pm | • | May 30 - May 30 | ||||||
| 1358 | 10:25 pm | 1:35 am | • | May 18 - Jun 8 | ||||||
| 1358 | 10:25 pm | 1:35 am | • | • | • | • | • | • | May 16 - Jun 10 |






