| Outbound | Return | Airlines | Shop | Baggage | Price | ||
|---|---|---|---|---|---|---|---|
| Chicago Boston | Outbound 04/21/25 1 Stopover (ATL) F91442, F93512 06h 13min | Return 05/19/25 1 Stopover (ATL) NK3381, NK1200 06h 53min |  Frontier Airlines |  | $114 | ||
| Best option Chicago Boston | Outbound 06/18/25 direct UA2444 02h 27min | Return 07/15/25 direct UA1414 02h 58min |  United Airlines |  | ? | $146 | |
| Chicago Boston | Outbound 04/12/25 1 Stopover (FLL) NK0002, NK0155 10h 40min | Return 04/27/25 2 Stopovers (ATL, MCO) NK0217, NK0456, NK0568 35h 59min |  Spirit Airlines |  | $151 | ||
| Chicago Boston | Outbound 04/21/25 1 Stopover (ATL) F91442, F93512 06h 13min | Return 05/19/25 1 Stopover (ATL) NK3381, NK1200 06h 53min | Frontier Airlines | | $117 | ||
| Chicago Boston | Outbound 04/21/25 1 Stopover (MCO) NK0573, NK0186 06h 41min | Return 05/19/25 1 Stopover (ATL) NK3381, NK1200 06h 53min | Spirit Airlines |  | $119 | ||
| Chicago Boston | Outbound 06/18/25 1 Stopover (JFK) B60906, B60618 04h 53min | Return 07/15/25 direct B60311 02h 55min |  JetBlue Airways |  | ? | $120 | |
| Chicago Boston | Outbound 04/21/25 1 Stopover (MCO) NK0573, NK0186 06h 41min | Return 05/19/25 1 Stopover (ATL) NK3381, NK1200 06h 53min | Spirit Airlines |  | $126 | ||
| Chicago Boston | Outbound 06/18/25 1 Stopover (JFK) B60906, B60618 04h 53min | Return 07/15/25 direct AA0598 02h 52min | JetBlue Airways |  | ? | $128 | |
| Chicago Boston | Outbound 06/18/25 direct UA2444 02h 27min | Return 07/15/25 direct UA1414 02h 58min | United Airlines |  | ? | $149 | |
| Chicago Boston | Outbound 06/18/25 1 Stopover (JFK) B60406, B61118 07h 50min | Return 07/15/25 direct B60311 02h 55min | JetBlue Airways |  | ? | $158 |
Airline
- JetBlue Airways
- United Airlines
- Frontier Airlines
- American Airlines
- Spirit Airlines
Tips and tricks to help you find cheap flights from Chicago to Boston
Favorite airline: Spirit Airlines
Flight tickets on the route Chicago – Boston are most frequently booked with Spirit Airlines.
Spirit Airlines
33 %
United Airlines
20 %
Delta
15 %
Direct flights are more expensive
On this route, direct flights are $13.00 more expensive than flights with a stopover.
non stop flight
1 stop
02h 30min
09h 23min
$160
$147
The favorite connection is non-stop
Flights from Chicago to Boston are most often booked as a direct flight.
Route
bookings
Direct flights
02h 30min, from $160
44 %
1 stopover Orlando International Airport, FL
09h 23min, from $147
15 %
1 stopover Minneapolis - St. Paul International Airport, MN
13h 44min, from $335
12 %
Important flight information
Flight information: Chicago - Boston
| Roundtrip from | $113.04 |
|---|---|
| Flight duration | min. 02:08 / max. 11:15 |
| Return flight duration | min. 02:45/ max. 06:55 |
| Distance | 1371 km |
| Flights per week | 153 |
| Departure airport | Airport Chicago-IL all Airports (ORD, MDW, RFD) (CHI) |
| Arrival airport | Airport Boston Logan International Airport, MA (BOS) |
| Destination country | Flights to United States |
Alternative routes to United States
- Flight Chicago - New York from $55
- Flight Chicago - Las Vegas from $141
- Flight Chicago - Los Angeles from $112
- Flight Chicago - Miami from $149
- Flight Chicago - San Francisco from $133
- Flight Chicago - Tampa from $98
- Flight Chicago - Denver from $81
- Flight Chicago - Orlando from $108
- Flight Chicago - New Orleans from $139
- Flight Chicago - Washington-DC from $130
Alternative flights to Boston
- Flight New York - Boston from $148
- Flight Miami - Boston from $76
- Flight New York - Boston from $164
- Flight Tampa - Boston from $80
- Flight Washington-DC - Boston from $116
- Flight Orlando - Boston from $86
- Flight Buffalo - Boston from $173
- Flight Los Angeles - Boston from $172
- Flight San Francisco - Boston from $228
- Flight Las Vegas - Boston from $174
Flight destinations with a similar price
- Flight Boston - Barcelona from $539
- Flight Boston - San Jose, Costa Rica from $356
- Flight Boston - Vienna from $573
- Flight Boston - Hamburg from $560
- Flight Boston - Dusseldorf from $613
- Flight Boston - Port au Prince from $541
- Flight Boston - Vancouver from $190
- Flight Boston - Stuttgart from $626
- Flight Boston - Toronto from $240
- Flight Boston - Cologne from $626
Flight destinations with a similar price
- Flight Chicago - Los Angeles from $112
- Flight Chicago - Orlando from $108
- Flight Chicago - Minneapolis from $109
- Flight Chicago - Phoenix - Sky Harbor from $108
- Flight Chicago - San Diego from $119
- Flight Chicago - Charlotte from $115
- Flight Chicago - St. Louis from $123
- Flight Chicago - Owensboro from $119