Exclusive Second City Vacation Deals
Second City vacation package deals
Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Hoffman Estates
Save 100% on your flight
per person
Jul 30 - Aug 4
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
per person
Aug 2 - Aug 7
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, laundry facilities, and concierge services are also on offer.
Hilton Garden Inn Chicago / Oak Brook
Save 100% on your flight
per person
Jul 10 - Jul 15
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
per person
Jul 18 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 24 - Aug 27
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.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
per person
Aug 3 - Aug 8
found 15 hours ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
This hotel features a restaurant, a gym, and a poolside bar. Enjoy the seasonal outdoor pool and perks like free WiFi. Self parking, a 24-hour business center, and a coffee shop are also offered.
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
$167 nightly
The price is $196 total per night
$196 total
Jun 3 - Jun 4
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$183 nightly
The price is $215 total per night
$215 total
Jun 29 - Jun 30
Total includes taxes and fees
A gym, valet parking, and concierge services are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 8 conference rooms, business center, and express check-out.
Pet friendly
Free WiFi
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$209 nightly
The price is $245 total per night
$245 total
Jun 29 - Jun 30
Total includes taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the gym, bar/lounge, and coffee shop.
Spa
Pet friendly
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.