Downtown Skokie Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Downtown Skokie Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
The Godfrey Hotel Chicago
Downtown Chicago
Price was $828, price is now $633 per person
$633
per person
Dec 31 - Jan 5
found 1 day ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, 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.
Hotel Riu Plaza Chicago
Downtown Chicago
Price was $1,309, price is now $869 per person
$869
per person
Dec 31 - Jan 5
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.
朝食が頂ける事が素晴らしく思う と共にそのアイテムも多数あり満足でしたが、連泊しておりますと少しずつアレンジを加えて頂けますと飽きがこないと思います。
Reviewed on Nov 12, 2026
Eurostars Magnificent Mile
Downtown Chicago
Price was $1,189, price is now $847 per person
$847
per person
Dec 31 - Jan 5
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.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $820, price is now $643 per person
$643
per person
Dec 31 - Jan 5
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.
Room was small, but clean and comfortable. Staff was super friendly and efficient. Great location! Short walking distance to several restaurants, bars and other attractions. Will definitely be staying there again!
Reviewed on Nov 12, 2026
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Downtown Chicago
Price was $843, price is now $674 per person
$674
per person
Dec 31 - Jan 5
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.
Hilton Garden Inn Chicago Downtown South Loop
Downtown Chicago
Price was $988, price is now $794 per person
$794
per person
Dec 31 - Jan 5
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 WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Soldier Field are located nearby.
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View all tripsTop Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
20.11 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
17.11 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
River Hotel
75 East Wacker Drive Chicago IL
18.88 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, room service, and a fitness center. Our guests praise the helpful staff and the clean ...
The Wade
644 N Lake Shore Dr Chicago IL
18.82 km from Downtown Skokie
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms ...
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
18.29 km from Downtown Skokie
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
Hilton Chicago
720 S Michigan Ave Chicago IL
20.35 km from Downtown Skokie
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean ...
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
172 W Adams St Chicago IL
19.31 km from Downtown Skokie
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 ...
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
18.9 km from Downtown Skokie
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the restaurant ...
Fairmont Chicago at Millennium Park
200 North Columbus Drive Chicago IL
19.25 km from Downtown Skokie
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms ...
Eurostars Magnificent Mile
660 North State Street Chicago IL
18.16 km from Downtown Skokie
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 ...
L7 Chicago by LOTTE
225 N Wabash Ave Chicago IL
18.97 km from Downtown Skokie
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 ...
The Godfrey Hotel Chicago
127 West Huron, at LaSalle Chicago IL
17.93 km from Downtown Skokie
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...
Freehand Chicago
19 East Ohio Street Chicago IL
18.4 km from Downtown Skokie
Stay at this hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. ...
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See all available properties in Downtown Skokie
View all propertiesLowest 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, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$247 Roundtrip, found 11 hours ago
$247
Roundtrip
found 11 hours ago
Tue, Jan 5 - Sat, Jan 23
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 11 hours ago
$257
Roundtrip
found 11 hours ago
Tue, Feb 23 - Wed, Mar 3
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$257 Roundtrip, found 15 hours ago
$257
Roundtrip
found 15 hours ago
Tue, Jan 26 - Tue, Feb 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$262 Roundtrip, found 21 hours ago
$262
Roundtrip
found 21 hours ago
Tue, Jan 26 - Tue, Feb 16
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$269 Roundtrip, found 21 hours ago
$269
Roundtrip
found 21 hours ago