Somers Vacations
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Somers Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
$514
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The staff was 10/10.
Reviewed on Oct 15, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
$751
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) 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.
Swissotel - Chicago
Downtown Chicago
$640
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Everyone was so nice and accommodating. The location is great. We had a great view of the river.
Reviewed on Oct 15, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
$565
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour health club, and valet parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Holiday Inn Express Chicago - Magnificent Mile by IHG
Downtown Chicago
$563
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Eurostars Magnificent Mile
Downtown Chicago
$703
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy free WiFi, a full-service spa, and a 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.
Top Hotel Deals
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 ...
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 ...
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 ...
Country Inn & Suites by Radisson Kenosha - Pleasant Prairie
7011 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 helpful staff and the clean ...
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. ...
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 ...
La Quinta Inn by Wyndham Milwaukee Airport / Oak Creek
7141 S 13th St Oak Creek WI
Book a stay at this business-friendly hotel in Oak Creek. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Antioch Hotel & Suites
350 Illinois 173 Antioch IL
Book a stay at this business-friendly hotel in Antioch. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. ...
Days Inn by Wyndham Waukegan
630 N Green Bay Road Waukegan IL
Stay at this motel in Waukegan. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Six Flags Great America and Gurnee Mills are located ...
Super 8 by Wyndham Sturtevant/Racine
910 S Sylvania Ave Sturtevant WI
Book a stay at this business-friendly hotel in Sturtevant. Enjoy free breakfast, free parking, and a 24-hour front desk. Our guests praise the helpful staff ...
Americas Best Value Inn & Suites Racine
5419 Durand Ave Mount Pleasant WI
Book a stay at this business-friendly hotel in Mount Pleasant. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the helpful staff in ...
The Stella Hotel & Ballroom
5706 8th Ave Kenosha WI
Book a stay at this business-friendly hotel in Kenosha. Enjoy free WiFi, free parking, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
WoodSpring Suites Gurnee - Chicago
5742 Northridge Drive Gurnee IL
Stay at this hotel in Gurnee. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Six Flags Great America and Gurnee Mills are located ...
Country Inn & Suites by Radisson, Mt. Pleasant-Racine West, WI
13339 Hospitality Court Mount Pleasant WI
Book a stay at this business-friendly hotel in Mount Pleasant. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
Comfort Inn Mount Pleasant – Racine
1150 Oakes Road Mount Pleasant WI
Book a stay at this business-friendly hotel in Mount Pleasant. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
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.
Thu, Nov 26 - Thu, Dec 3
DEN
Denver Intl.
MKE
General Mitchell Intl.
$257
Roundtrip
found 2 days ago
Fri, Nov 27 - Mon, Nov 30
DEN
Denver Intl.
MKE
General Mitchell Intl.
$274
Roundtrip
found 2 days ago
Tue, Nov 17 - Thu, Nov 26
MCO
Orlando Intl.
MKE
General Mitchell Intl.
$349
Roundtrip
found 2 hours ago
Tue, Nov 24 - Wed, Dec 2
DEN
Denver Intl.
MKE
General Mitchell Intl.
$357
Roundtrip
found 2 days ago
Mon, Nov 23 - Thu, Nov 26
SEA
Seattle - Tacoma Intl.
MKE
General Mitchell Intl.
$368
Roundtrip
found 1 hour ago
Best points of interest in Kenosha
- Six Flags Great America Vacations
- Lake Michigan Vacations
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- Illinois Beach State Park Vacations
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- Great Wolf Lodge Water Park Vacations
- Pleasant Prairie RecPlex Vacations
- Wilmot Mountain Vacations
- University of Wisconsin-Parkside Vacations
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