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Second City Vacation Packages

Second City Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 - Chicago, IL
Courtyard by Marriott Chicago Schaumburg/Woodfield Mall
Holiday Inn Chicago-Oakbrook by IHG
Holiday Inn Chicago - Schaumburg by IHG
Hotel Riu Plaza Chicago
Viceroy Chicago
theWit Chicago, a Hilton Hotel
Thompson Chicago, by Hyatt
Level Chicago Fulton Market
Hilton Chicago O'Hare Airport
Trump International Hotel & Tower Chicago
Sofitel Chicago Magnificent Mile

3-4 Night Vacations in Second City

Price found within the past 48 hours. Click for updated prices.
Grand Royal Hotel O'Hare - Chicago
Hotel Riu Plaza Chicago
Trump International Hotel & Tower Chicago
Pendry Chicago

5-7 Night Vacations in Second City

Price found within the past 48 hours. Click for updated prices.
DoubleTree Suites by Hilton Htl & Conf Cntr Downers Grove
Park Hyatt Chicago
Pendry Chicago
Hotel Riu Plaza Chicago

Second City Last Minute Hotel Deals

Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful ...
Hilton Chicago/Magnificent Mile Suites
Claridge House

Claridge House

4 out of 5
1244 N Dearborn Parkway, Chicago, IL
Stay at this 4-star spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful ...
Claridge House
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
105 E Delaware Pl, Chicago, IL
Stay at this 3.5-star boutique hotel in Chicago. Enjoy free breakfast, free WiFi, and a fitness center. Our guests praise the restaurant and the helpful staff ...
The Whitehall Hotel, BW Premier Collection
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy, Chicago, IL
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
The Chicago Hotel Collection Ambassador Gold Coast
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Stay at this 4-star hotel in Chicago. Enjoy free WiFi, room service, and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. ...
Freehand Chicago
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
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

3 out of 5
201 East Walton Place, Chicago, IL
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 ...
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
Hotel Lincoln

Hotel Lincoln

4 out of 5
1816 N Clark Street, Chicago, IL
Stay at this 4-star boutique hotel in Chicago. Enjoy a rooftop terrace, a 24-hour fitness center, and WiFi (surcharge). Our guests praise the bar and the helpful ...
Hotel Lincoln
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.