Exclusive Second City Vacation Deals
Second City vacation package deals
Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. A hair salon, WiFi in public areas, and luggage storage are also on offer.
The French Country Inn Lake Geneva
Save 100% on your flight
per person
Jul 3 - Jul 7
found 1 day ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
A private beach and a restaurant are featured at this smoke-free hotel. There's no skimping on freebies - guests receive free continental breakfast, free WiFi, and free self parking. A picnic area, luggage storage, and concierge services are also on offer.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. A lobby fireplace, a communal living room, and express check-out are also on offer.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
La Banque Hotel
Save 100% on your flight
per person
Jul 3 - Jul 6
found 19 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the 24-hour business center. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and concierge services.
Hilton Garden Inn Hoffman Estates
per person
Jul 30 - Aug 4
found 2 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A coffee shop, a grocery/convenience store, and a lobby fireplace are also on offer.
Frequently asked questions
Top Second City hotel deals
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$153 nightly
The price is $179 total per night
$179 total
May 28 - May 29
Total includes taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. A coffee shop, a snack bar/deli, and a lobby fireplace are also on offer.
Pet friendly
Free WiFi
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$126 nightly
The price is $148 total per night
$148 total
May 28 - May 29
Total includes taxes and fees
This hotel features a 24-hour gym and a bar/lounge. Families will appreciate the onsite laundry facilities and babysitting. Traveling on business? Take advantage of the 24-hour business center, express check-out, and valet parking.
Air conditioning
Gym
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$134 nightly
The price is $157 total per night
$157 total
May 28 - May 29
Total includes taxes and fees
This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.
Free WiFi
Restaurant
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.