Vacations Close To Skydeck Ledge

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Skydeck Ledge Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was $802, price is now $628 per person
$628
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,530, price is now $998 per person
$998
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)
We stayed for one night and everything from the staff to the room was absolutely perfect. We definitely would stay here again.

Reviewed on Oct 29, 2026

The Talbott, Autograph Collection

The Talbott, Autograph Collection

4.5 out of 5
Downtown Chicago
Price was $1,115, price is now $800 per person
$800
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)
Staff was great and the room was clean!

Reviewed on Oct 29, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,082, price is now $799 per person
$799
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was $1,097, price is now $857 per person
$857
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $1,314, price is now $1,027 per person
$1,027
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was $1,202, price is now $946 per person
$946
per person
Dec 1 - Dec 5
found 12 hours ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)
Rooms are very small. You will need to call down for them to bring up a refrigerator. Other than that, everything was okay.

Reviewed on Oct 29, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was $1,087, price is now $856 per person
$856
per person
Dec 1 - Dec 5
found 23 hours ago
Roundtrip flight included
Little Rock (LIT) to Chicago (ORD)

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Best Lodging Options Near Skydeck Ledge

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
0.98 km from Skydeck Ledge
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 MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
172 W Adams St Chicago IL
0.2 km from Skydeck Ledge
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 ...
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
1.27 km from Skydeck Ledge
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 ...
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
0.34 km from Skydeck Ledge
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
1.11 km from Skydeck Ledge
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 ...
Central Loop Hotel

Central Loop Hotel

4 out of 5
111 West Adams Street Chicago IL
0.35 km from Skydeck Ledge
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful staff ...
Hyatt Place Chicago/Downtown - The Loop

Hyatt Place Chicago/Downtown - The Loop

3 out of 5
28 North Franklin Street Chicago IL
0.44 km from Skydeck Ledge
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the breakfast ...
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St Chicago IL
0.65 km from Skydeck Ledge
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff ...
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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.