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Skydeck Ledge Vacation Packages

Skydeck Ledge Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Four Points by Sheraton Chicago Westchester/Oak Brook

Four Points by Sheraton Chicago Westchester/Oak Brook

3 out of 5
Price was $361, price is now $253 per person
$253
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3-star business-friendly hotel in Westchester. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Oak Brook Golf Course and Graue Mill and Museum are located nearby.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Save 100% on your flight
Price was $1,217, price is now $595 per person
$595
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free breakfast, free WiFi, and 2 bars/lounges. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Save 100% on your flight
Price was $1,154, price is now $610 per person
$610
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
The Emily Hotel

The Emily Hotel

4 out of 5
Save 100% on your flight
Price was $1,141, price is now $645 per person
$645
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star business-friendly 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 United Center and Chicago Riverwalk are located nearby.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Save 100% on your flight
Price was $1,784, price is now $1,049 per person
$1,049
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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

Level Chicago Fulton Market

4 out of 5
Save 100% on your flight
Price was $1,137, price is now $682 per person
$682
per person
Nov 25 - Dec 2
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, an outdoor pool, and parking (surcharge). Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Save 100% on your flight
Price was $801, price is now $498 per person
$498
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Save 100% on your flight
Price was $628, price is now $392 per person
$392
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Save 100% on your flight
Price was $692, price is now $437 per person
$437
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4-star 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Save 100% on your flight
Price was $1,061, price is now $685 per person
$685
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The Langham, Chicago

The Langham, Chicago

5 out of 5
Save 100% on your flight
Price was $1,490, price is now $963 per person
$963
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 5-star 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.
Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
Save 100% on your flight
Price was $767, price is now $499 per person
$499
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.

3-4 Night Vacations in Skydeck Ledge

Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $570, price is now $346 per person
$346
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $872, price is now $466 per person
$466
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,784, price is now $1,049 per person
$1,049
per person
Nov 26 - Nov 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $628, price is now $392 per person
$392
per person
Nov 25 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

5-7 Night Vacations in Skydeck Ledge

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove

4 out of 5
Price was $472, price is now $272 per person
$272
per person
Nov 28 - Dec 3
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was $2,618, price is now $1,654 per person
$1,654
per person
Nov 13 - Nov 20
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,217, price is now $595 per person
$595
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,154, price is now $610 per person
$610
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)

Skydeck Ledge Last Minute Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Congress Plaza Hotel
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
171 W Randolph St, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy breakfast (surcharge), a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar ...
The Allegro Royal Sonesta Hotel Chicago Loop
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
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 Midland Hotel Chicago, a Tribute Portfolio Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. ...
Embassy Suites by Hilton Chicago Downtown River North
Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

3 out of 5
350 West Wolf Point Plaza, Building 2, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the ...
Holiday Inn Chicago Dwtn - The Mart by IHG
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Stay at this 4-star luxury hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff ...
Palmer House a Hilton Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the restaurant and the helpful ...
Club Quarters Hotel, Central Loop, Chicago
Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop

3 out of 5
245 S Franklin St, Chicago, IL
Stay at this 3-star business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and ...
Hilton Garden Inn Chicago Central Loop
See all 4,024 properties in Skydeck Ledge
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.