Lodging Image

Southwest Side, Chicago hotel rooms at the Destination Hotels

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Oct 3 - Oct 4
Tomorrow
Oct 4 - Oct 5
Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18
Save an average of 15% on thousands of hotels when you're signed in

Top Southwest Side Hotel Reviews

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

10/10 Excellent
"Spacious room. Great location."
Keith 4-night trip
Posted 1 hour ago
The Royal Sonesta Chicago Downtown
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

10/10 Excellent
"Room is pretty dim, so you really have to utilize all the lights in the room for it to be bright! Gym on the second floor is very nice, bed is comfy, TV had local channels, really love the desk as I was able to study and get some admin work done. Overall good pick! There's free tea and water in lobby as needed."
Darnetta 2-night trip
Posted 1 hour ago
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
Eurostars Magnificent Mile

Eurostars Magnificent Mile

10/10 Excellent
"."
GARY 2-night trip
Posted 1 hour ago
Eurostars Magnificent Mile
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent
"I took a chance on this hotel and I am glad I did. It was right in the center of EVERYTHING! We rented a car, but never drove it because everything we wanted to see and do was within walking distance. I paid for the upgrade and was able to check in early, which was perfect considering my flight arrived at 7:55AM. We had free breakfast, two cocktails daily & 4 bottles of water per day, along with late check out. However, the only drawback was we had no hot water the entire 4 days I was there. They managed to fix it and we had one night of hot water, but every day after was luke warm. Overall it was a great stay, location and experience."
Kosha 3-night trip
Posted 1 hour ago
The Chicago Hotel Collection - Magnificent Mile
Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

10/10 Excellent
"Clean and quite."
Jacqueline 3-night trip
Posted 1 hour ago
Sports Illustrated Resorts Chicago
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

10/10 Excellent
"Great hotel - great rooms - nice restaurant and bar"
Carrie 1-night trip
Posted 6 hours ago
The Godfrey Hotel Chicago
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"The hotel was a very convenient location from downtown and Lake Michigan. Definitely one of the better breakfasts I've had recently and the pricing sits just right for the amenities and convenience this hotel offers"
Sudeep 1-night trip
Posted 14 hours ago
The Chicago Hotel Collection Ambassador Gold Coast
Freehand Chicago

Freehand Chicago

10/10 Excellent
"We absolutely enjoyed our stay at the Kins Hotel. Our room was exceptionally clean, spacious and comfortable, and it was actually much larger than the images we had seen when booking, which was a lovely surprise. The staff were amazing and couldn’t have been more helpful or friendly. From the reception staff and valet team to the cleaners, everyone was welcoming, professional and always happy to assist whenever we had a question. Overall, we had a fantastic stay at the Kins Hotel and wouldn’t hesitate to recommend it to anyone looking for a great place to stay. We would happily return ourselves!"
Paul 1-night trip
Posted 2 days ago
Freehand Chicago

Explore a world of travel with Expedia