Trevor Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Trevor 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.
Front desk staff unfriendly and somewhat rude. We put sign to clean room and left in the morning and returned around 3:00 PM and room was still not clean. I called service desk and he apologized and said they’re just too busy and will come by 5:30PM. When they did show up we had to leave the room and wait for them to finish. Unacceptable!!!!!
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
Harbor Shores on Lake Geneva
300 Wrigley Dr Lake Geneva WI
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the pool and the helpful staff ...
Timber Ridge Lodge and Waterpark
7020 Grand Geneva Way Lake Geneva WI
Book a stay at this spa aparthotel in Lake Geneva. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
Great Wolf Lodge Illinois
1700 Nations Dr Gurnee IL
Book a stay at this family-friendly resort in Gurnee. Enjoy 6 indoor pools, 5 restaurants, and 2 bars/lounges. Our guests praise the helpful staff in our reviews. ...
La Quinta Inn & Suites by Wyndham Chicago Gurnee
5688 Northridge Rd Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Grand Geneva Resort & Spa
7036 Grand Geneva Wy Lake Geneva WI
Book a stay at this spa resort in Lake Geneva. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
The Cove Of Lake Geneva
111 Center St Lake Geneva WI
Book a stay at this family-friendly hotel in Lake Geneva. Enjoy an outdoor pool, 2 hot tubs, and room service. Our guests praise the pool and the helpful staff ...
Lodge Geneva National
W4240 WI-50 Lake Geneva WI
Book a stay at this golf resort in Lake Geneva. Enjoy an outdoor pool, breakfast (surcharge), and a fitness center. Our guests praise the pool and the restaurant ...
Sonesta ES Suites Chicago Waukegan Gurnee
1440 S White Oak Dr Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Holiday Inn Club Vacations at Lake Geneva Resort by IHG
7036 Grand Geneva Way Lake Geneva WI
Book a stay at this spa resort in Lake Geneva. Enjoy free parking, an outdoor pool, and a full-service spa. Our guests praise the helpful staff in our reviews. ...
DoubleTree by Hilton Libertyville - Mundelein
510 E IL Route 83 Mundelein IL
Book a stay at this business-friendly hotel in Mundelein. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Hampton Inn Chicago - Gurnee
5550 Grand Ave Gurnee IL
Book a stay at this business-friendly hotel in Gurnee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Best Western Executive Inn Kenosha/Pleasant Prairie
7220 122nd Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
The Inn on Sheridan
2723 Sheridan Rd Zion IL
Book a stay at this business-friendly hotel in Zion. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms ...
Red Roof Inn Gurnee - Waukegan
3031 Belvidere Rd Waukegan IL
Book a stay at this business-friendly hotel in Waukegan. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the ...
Days Inn by Wyndham Pleasant Prairie Kenosha
7540 118th Ave Pleasant Prairie WI
Book a stay at this family-friendly hotel in Pleasant Prairie. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the ...
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.
Mon, Nov 2 - Tue, Nov 17
ATL
Hartsfield-Jackson Atlanta Intl.
MKE
General Mitchell Intl.
$215
Roundtrip
found 1 day ago
Tue, Sep 29 - Sat, Oct 3
TPA
Tampa Intl.
MKE
General Mitchell Intl.
$297
Roundtrip
found 2 days ago
Tue, Sep 29 - Tue, Oct 13
SEA
Seattle - Tacoma Intl.
MKE
General Mitchell Intl.
$327
Roundtrip
found 4 days ago
Tue, Sep 29 - Fri, Oct 2
TPA
Tampa Intl.
MKE
General Mitchell Intl.
$335
Roundtrip
found 2 days ago
Tue, Nov 24 - Wed, Dec 2
SEA
Seattle - Tacoma Intl.
MKE
General Mitchell Intl.
$357
Roundtrip
found 3 days ago
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