Find Cheap Flights from Boston (BOS) to Chicago (CHI) from CHF 286

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Selected flight deals from Boston to Chicago

The lowest prices found within the past 7 days from Boston to Chicago were CHF 56 for one-way flights and CHF 286 for return flights, for the period specified. Prices and availability are subject to change. Additional terms apply.

Mon, 1 Dec - Tue, 2 Dec
BOS
Logan Intl.
ORD
O'Hare Intl.
CHF 286 Return, found 21 hours ago
CHF 286
Return
found 21 hours ago
Select Delta flight, departing Mon, 1 Dec from Logan Intl. to O'Hare Intl., returning Tue, 2 Dec, priced at CHF 286 found 21 hours ago
Mon, 1 Dec - Tue, 2 Dec
BOS
Logan Intl.
ORD
O'Hare Intl.
CHF 294 Return, found 21 hours ago
CHF 294
Return
found 21 hours ago
Select Delta flight, departing Mon, 1 Dec from Logan Intl. to O'Hare Intl., returning Tue, 2 Dec, priced at CHF 294 found 21 hours ago
Mon, 1 Dec - Tue, 2 Dec
BOS
Logan Intl.
ORD
O'Hare Intl.
CHF 310 Return, found 21 hours ago
CHF 310
Return
found 21 hours ago
Select American Airlines flight, departing Mon, 1 Dec from Logan Intl. to O'Hare Intl., returning Tue, 2 Dec, priced at CHF 310 found 21 hours ago
Mon, 1 Dec - Tue, 2 Dec
BOS
Logan Intl.
ORD
O'Hare Intl.
CHF 317 Return, found 21 hours ago
CHF 317
Return
found 21 hours ago
Select Delta flight, departing Mon, 1 Dec from Logan Intl. to O'Hare Intl., returning Tue, 2 Dec, priced at CHF 317 found 21 hours ago
Mon, 1 Dec - Tue, 2 Dec
BOS
Logan Intl.
ORD
O'Hare Intl.
CHF 320 Return, found 21 hours ago
CHF 320
Return
found 21 hours ago
Select JetBlue Airways flight, departing Mon, 1 Dec from Logan Intl. to O'Hare Intl., returning Tue, 2 Dec, priced at CHF 320 found 21 hours ago
Cheap Flights from Boston to Chicago & Flight Information
Origin airport IATA code
BOS
Destination airport IATA code
ORD
Number of flight options
3
Return price
CHF 285
Average flight time
1 hour 59 mins

Best Day to Book Flight from Boston to Chicago

Chicago Flight Information

Traveling From
Boston
Origin Airport IATA Code
BOS
Traveling To
Chicago
Destination Airport IATA Code
CHI
Number of Airlines Serving
Available Airlines
JetBlue Airways, Delta, United, American Airlines
Distance
Direct Flight Time
Flight Price
CHF 286

Need a car after flight from Boston to Chicago

Economy

Chevrolet Spark or similar
  • 4 people
Chevrolet Spark
Economy Chevrolet Spark

Compact

Ford Focus or similar
  • 4 people
Ford Focus
Compact Ford Focus

Midsize

Toyota Corolla or similar
  • 5 people
Toyota Corolla
Midsize Toyota Corolla

SUV

Jeep Compass or similar
  • 5 people
Jeep Compass
SUV Jeep Compass

Place to stay after flight from Boston to Chicago

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Dieses Hotel im luxuriösen Stil bietet dir einen angenehmen Aufenthalt in Chicago. Freu dich auf Wellnessbereich, Frühstück (gegen Gebühr) und Fitnesscenter ...
8.4/10 Very Good! (2,077 reviews)
Room great, lobby bar the best! Christmas tree gorgeous. And free brownie a nice touch!

Reviewed on 22 Nov 2025

Opens in a new windowPalmer House a Hilton Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Dieses Hotel bietet dir einen angenehmen Aufenthalt in Chicago. Freu dich auf inbegriffenes Frühstück, Zimmerservice (bitte Zeiten beachten) und Fitnessmöglichkeiten. ...
8.4/10 Very Good! (5,289 reviews)
All above.

Reviewed on 24 Nov 2025

Opens in a new windowEmbassy Suites by Hilton Chicago Downtown River North
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Dieses Hotel für Geschäftsreisende bietet dir einen angenehmen Aufenthalt in Chicago. Freu dich auf 2 Restaurants, 2 Bars/Lounges und Frühstück (gegen Gebühr). ...
8/10 Very Good! (9,636 reviews)
Thanks

Reviewed on 23 Nov 2025

Opens in a new windowCongress Plaza Hotel
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Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Dieses Hotel für Geschäftsreisende bietet dir einen angenehmen Aufenthalt in Chicago. Freu dich auf Fitnessmöglichkeiten, Parkservice (kostenpflichtig) und eine ...
8.8/10 Excellent! (3,374 reviews)
Hotel location was very convenient to restaurants and attractions. Room was in need of some repairs .

Reviewed on 25 Nov 2025

Opens in a new windowHilton Chicago/Magnificent Mile Suites
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place Chicago IL
Dieses Hotel für Geschäftsreisende bietet dir einen angenehmen Aufenthalt in Chicago. Freu dich auf WLAN-Internetzugang (kostenlos), Frühstück (gegen Gebühr) ...
9.2/10 Wonderful! (4,063 reviews)
Great location and great price for a quick overnight trip.

Reviewed on 21 Nov 2025

Opens in a new windowcitizenM Chicago Downtown
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Dieses Hotel für Geschäftsreisende bietet dir einen angenehmen Aufenthalt in Chicago. Freu dich auf 2 Restaurants, Frühstück (gegen Gebühr) und Flughafentransfer. ...
8.2/10 Very Good! (2,182 reviews)
Convenient. Wonderful staff. Expensive!

Reviewed on 27 Nov 2025

Opens in a new windowHilton Chicago O'Hare Airport
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Savings based on all holiday package bookings with Flight + Hotel made on ebookers.ie from January 1, 2019 to December 31, 2019 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.