Cambridge Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Cambridge Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
$767
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Nice Stay wifi was ok really not working well once you step out of the hotel better control
Reviewed on Sep 11, 2026
Trump International Hotel & Tower Chicago
Downtown Chicago
$1,204
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago Fulton Market
Downtown Chicago
$928
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Stay at this hotel in Chicago. Enjoy free WiFi, an outdoor pool, and a fitness center. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Level Chicago – Old Town
Downtown Chicago
$793
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this family-friendly aparthotel in Chicago. Enjoy free WiFi, an outdoor pool, and a rooftop terrace. Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The Talbott, Autograph Collection
Downtown Chicago
$803
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
$1,042
per person
Nov 3 - Nov 7
found 1 day ago
Roundtrip non-stop flight included
Norfolk (ORF) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Navy Pier and Michigan Avenue are located nearby.
The hotel was amazing and it had the best view of Chicago skyline and lake views. The rooftop restaurant was beautiful and navy pier at your front door. I’m looking forward to returning soon.
Reviewed on Sep 11, 2026
Top Hotel Deals
The Madison Concourse Hotel and Governor's Club
1 W Dayton St Madison WI
Book a stay at this luxury hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the breakfast and the pool ...
Baymont Inn & Suites by Wyndham Madison
2810 Coho Street Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
DoubleTree by Hilton Madison Downtown
525 West Johnson Street Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a free airport shuttle. Our guests praise the helpful staff ...
DoubleTree by Hilton Madison East
4402 E Washington Ave Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
La Quinta Inn & Suites by Wyndham Madison American Center
5217 E Terrace Dr Madison WI
Stay at this hotel in Madison. Enjoy free parking, a fitness center, and WiFi (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. ...
The Dylin
611 E Dayton St Madison WI
Stay at this aparthotel in Madison. Enjoy free WiFi, a 24-hour fitness center, and parking (surcharge). Popular attractions Capitol Square and Camp Randall Stadium ...
Best Western Premier Park Hotel
22 S Carroll Street Madison WI
Book a stay at this spa hotel in Madison. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms ...
The Edgewater
1001 Wisconsin Place Madison WI
Book a stay at this luxury hotel in Madison. Enjoy a full-service spa, 4 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Embassy Suites By Hilton Madison Downtown
231 S. Pinckney Street Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free WiFi, and room service. Popular attractions Capitol Square and Camp Randall Stadium are located ...
Moxy Madison Downtown
823 East Washington Ave Madison WI
Stay at this hotel in Madison. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Popular attractions Capitol Square and Camp Randall Stadium are ...
AmericInn by Wyndham Madison South
101 W Broadway Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free parking, and a sauna. Our guests praise the breakfast and the helpful staff ...
Motel 6 Madison, WI - East
4202 E Towne Blvd Madison WI
Stay at this motel in Madison. Enjoy free parking, a 24-hour front desk, and daily housekeeping. Our guests praise the helpful staff and the clean rooms in our ...
Best Western Plus InnTowner Madison
2424 University Avenue Madison WI
Stay at this hotel in Madison. Enjoy free breakfast, free parking, and a free area shuttle. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hilton Garden Inn Madison Downtown
770 Regent Street Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy breakfast (surcharge), a 24-hour fitness center, and parking (surcharge). Our guests praise the ...
Fairfield by Marriott Inn & Suites Madison South
722 John Nolen Drive Madison WI
Book a stay at this business-friendly hotel in Madison. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Oct 6 - Tue, Oct 20
PDX
Portland Intl.
MSN
Dane County Regional
$351
Roundtrip
found 5 days ago
Sat, Sep 26 - Thu, Oct 1
SEA
Seattle - Tacoma Intl.
MSN
Dane County Regional
$368
Roundtrip
found 6 days ago
Fri, Nov 13 - Tue, Nov 17
BOS
Logan Intl.
MSN
Dane County Regional
$377
Roundtrip
found 4 days ago
Wed, Sep 23 - Sat, Oct 10
SEA
Seattle - Tacoma Intl.
MSN
Dane County Regional
$409
Roundtrip
found 3 days ago
Wed, Sep 23 - Sat, Oct 10
SEA
Seattle - Tacoma Intl.
MSN
Dane County Regional
$599
Roundtrip
found 3 days ago
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