Vacations Close To Second City
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Second City Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Motel Edgebrook Chicago North Shore by OYO
Forest Glen
Price was $918, price is now $723 per person
$723
per person
Dec 24 - Jan 1
found 7 hours ago
Roundtrip non-stop flight included
San Diego (SAN) to Chicago (ORD)
Everything was good for the price and super easy to go to the downtown
Reviewed on Nov 11, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was $1,059, price is now $817 per person
$817
per person
Dec 21 - Dec 28
found 12 hours ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Charged for an extra night that we didn’t stay and called and was told a reimbursement was completed. Five days later, the full charge for the night we didn’t stay posted in my account and with no reimbursement. When I called again, was told there was nothing they could do because the reimbursement was “released” and I would have to wait to talk to a manager when they arrived which would not be until the nighttime hours.
Reviewed on Nov 14, 2026
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View all tripsBest Lodging Options Near Second City
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
0.82 km from Second City
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the helpful ...
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
4.12 km from Second City
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 Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
2.01 km from Second City
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in ...
River Hotel
75 East Wacker Drive Chicago IL
2.74 km from Second City
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 ...
The Godfrey Hotel Chicago
127 West Huron, at LaSalle Chicago IL
1.86 km from Second City
Book a stay at this luxury hotel in Chicago. Enjoy a full-service spa, a rooftop terrace, and a 24-hour fitness center. Our guests praise the helpful staff and ...
The Chicago Hotel Collection River North
312 W. Chestnut St. Chicago IL
1.44 km from Second City
Stay at this hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. ...
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.