$55 Cheap flight deals from Chicago (CHI) to Cambridge (BOS)

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This Weekend's Flight Deals from Chicago to Cambridge

This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Fri, Apr 25 - Mon, Apr 28
MDW
Midway Intl.
BOS
Logan Intl.
$325 Roundtrip, found 15 hours ago
$325
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Fri, Apr 25 from Midway Intl. to Logan Intl., returning Mon, Apr 28, priced at $325 found 15 hours ago
Fri, Apr 25 - Fri, May 2
ORD
O'Hare Intl.
BOS
Logan Intl.
$335 Roundtrip, found 1 hour ago
$335
Roundtrip
found 1 hour ago
Select Spirit Airlines flight, departing Fri, Apr 25 from O'Hare Intl. to Logan Intl., returning Fri, May 2, priced at $335 found 1 hour ago

Airfares from $55 One Way, $109 Round Trip from Chicago to Cambridge

Prices starting at $109 for return flights and $55 for one-way flights to Cambridge were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.

Wed, May 7 - Wed, May 14
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 1 day ago
$109
Roundtrip
found 1 day ago
Select JetBlue Airways flight, departing Wed, May 7 from Chicago to Boston, returning Wed, May 14, priced at $109 found 1 day ago
Thu, Oct 23 - Thu, Oct 30
ORD
Chicago
BOS
Boston
$109 Roundtrip, found 20 hours ago
$109
Roundtrip
found 20 hours ago
Select Spirit Airlines flight, departing Thu, Oct 23 from Chicago to Boston, returning Thu, Oct 30, priced at $109 found 20 hours ago
Sat, Oct 18 - Thu, Oct 30
ORD
Chicago
BOS
Boston
$113 Roundtrip, found 10 hours ago
$113
Roundtrip
found 10 hours ago
Select American Airlines flight, departing Sat, Oct 18 from Chicago to Boston, returning Thu, Oct 30, priced at $113 found 10 hours ago
Fri, Jul 25 - Mon, Jul 28
MDW
Chicago
BOS
Boston
$117 Roundtrip, found 13 hours ago
$117
Roundtrip
found 13 hours ago
Select Southwest Airlines flight, departing Fri, Jul 25 from Chicago to Boston, returning Mon, Jul 28, priced at $117 found 13 hours ago
Tue, Jul 22 - Wed, Jul 30
ORD
Chicago
BOS
Boston
$117 Roundtrip, found 1 hour ago
$117
Roundtrip
found 1 hour ago
Select American Airlines flight, departing Tue, Jul 22 from Chicago to Boston, returning Wed, Jul 30, priced at $117 found 1 hour ago

Cambridge economy flight packages

Price found within the past 48 hours. Click for updated prices.
The Revolution Hotel
3.5-star property

The Revolution Hotel

8.8/10 Excellent! (1,968 reviews)

May 22 - May 27

5 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Stayed in King Room with shared bathroom down hall. Bathrooms were clean. Adequate towels were available. Staff were super friendly and helpful.

Reviewed on Oct 11, 2024

Meco Hotel
2.0-star property

Meco Hotel

8.4/10 Very Good! (118 reviews)

Jun 7 - Jun 12

5 night stay

Chicago (CHI) to Boston (BOS)

Southwest Airlines • Roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Loved it, thank you Meco Hotel!

Reviewed on Mar 29, 2025

YOTEL Boston
4.0-star property

YOTEL Boston

8.6/10 Excellent! (1,978 reviews)

May 22 - May 27

5 night stay

Chicago (CHI) to Boston (BOS)

JetBlue Airways • Non-stop roundtrip • Coach
Save 100% on your flight
per person
found 1 day ago
Convenient. Clean. Close to shops and restaurants in the seaport.

Reviewed on Jan 29, 2025

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Cambridge first class flight packages

Price found within the past 48 hours. Click for updated prices.
The Cove At Salem
3.0-star property

The Cove At Salem

9.4/10 Exceptional! (459 reviews)

Jun 8 - Jun 12

4 night stay

Chicago (ORD) to Boston (BOS)

American Airlines • Roundtrip • FirstClass
per person
found 11 hours ago
The Forbidden Forest room exceeded our expectations! A truly unique experience. Only wish was that there was a darker curtain on the window.

Reviewed on Apr 10, 2025

Fairmont Copley Plaza, Boston
4.5-star property

Fairmont Copley Plaza, Boston

8.8/10 Excellent! (1,006 reviews)

Jun 8 - Jun 12

4 night stay

Chicago (ORD) to Boston (BOS)

United • FirstClass

Boston (BOS) to Chicago (ORD)

American Airlines • FirstClass
per person
found 11 hours ago
Valet parking rate of $72/night was excessive. Other than that, the room was lovely and comfortable for our family of 5, staff was responsive and friendly. Gym is well equipped with nice views. Very convenient to get to Logan airport from this hotel.

Reviewed on Apr 14, 2025

The Whitney Hotel
4.0-star property

The Whitney Hotel

9.6/10 Exceptional! (384 reviews)

Jun 8 - Jun 12

4 night stay

Chicago (ORD) to Boston (BOS)

United • FirstClass

Boston (BOS) to Chicago (ORD)

American Airlines • FirstClass
per person
found 11 hours ago
What a gem in Boston! I've been to Boston many times and usually stay closer to the Downtown Crossing area. This time we stayed at the Whitney, choosing to try out that part of town. We loved it! Bigger than a boutique hotel, but small enough to feel intimate. Charles St is a great walking street, and we loved the location. The room was on the ground level (actually partly below ground) but was excellent! Well-appointed room, a good amount of space for Boston, and super professional staff. I'll be back when I come back to Boston

Reviewed on Jul 30, 2024

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More About Flying To Cambridge from Chicago

Route Information for Flights from Chicago to Cambridge

Origin Airport IATA Code
CHI
Destination Airport IATA Code
BOS
Distance
Direct Flight Airlines
Earliest Flight Arrival
Latest Flight Arrival

Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.

Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.