A cityscape with a prominent building with a green dome, surrounded by greenery and a body of water.

Search Lakeside Hotels in South Side

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on South Side Lakeside Hotels

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
Next weekend
9 Oct - 11 Oct
In two weeks
16 Oct - 18 Oct

Our top choices for South Side hotels on the lake

A modern lobby with a sofa, coffee table, and a fireplace.
A bar area with a counter, multiple TVs, and a seating area with chairs and tables.
A casino floor with multiple slot machines and a few blackjack tables.
A modern hotel lobby with a coffee station, seating area, and a reception desk.

1. Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago
East Chicago
United States
WENLIN
£114
includes taxes & fees
5 Oct - 6 Oct
Ameristar Casino Hotel East Chicago
An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
A waterfront cityscape with modern buildings, a Ferris wheel, and several cruise ships docked.
A view from a room with a large window overlooking a cityscape at night, featuring a river and illuminated buildings.
A modern living room with a large window overlooking a body of water, a tripod, and a sofa.

2. Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
United States
Shanequa
£232
includes taxes & fees
4 Oct - 5 Oct
Sable at Navy Pier Chicago, Curio Collection by Hilton
A banquet hall with round tables, chairs, and chandeliers.
A gym with treadmills, elliptical machines, and weight stations.
A hotel room with a large bed, a desk, a chair, a lamp, and a view of trees through the window.
A hotel room with two beds, a desk, a chair, a TV, and a large window with a view of trees.

3. Hyatt Lodge Oak Brook Chicago

Hyatt Lodge Oak Brook Chicago
Oak Brook
United States
wayne b
£133
includes taxes & fees
1 Nov - 2 Nov
Hyatt Lodge Oak Brook Chicago
A person pouring champagne into a glass near a window overlooking a cityscape with a Ferris wheel.
A modern bar area with high stools, a bar counter, and shelves of liquor bottles.
A modern hotel lobby with a marble floor, seating areas, and a ceiling with a sky-like projection.
A modern hotel room with a large window offering a view of the sea and a cityscape. There is a seating area with a sofa and a small table.

4. The Wade

The Wade
Downtown Chicago
United States
Erin
£127
includes taxes & fees
1 Nov - 2 Nov
The Wade
A cityscape with high-rise buildings, a marina, and a waterfront.
A spacious indoor area with multiple tables and chairs, large windows, and a bar area.
An outdoor seating area with fire pits, cushioned seating, and a glass building facade.
A modern hotel lobby with a sectional sofa, round tables, and chairs, a flat-screen TV, and large windows offering city views.

5. Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago
South Loop
United States
Tony
£273
includes taxes & fees
1 Nov - 2 Nov
Hyatt Regency McCormick Place Chicago
A rooftop terrace with a brick wall, large windows, and a metal railing.
A beach with a sandy shore and calm sea.
A modern kitchen with white cabinets, a dining area with a blue sofa and orange cushions, and a large window providing natural light.
A hotel room with a bed, a desk, a chair, a lamp, a window with curtains, and a cityscape painting on the wall.

6. Artistic Loft Rooftop | 13 mins DT | 4 mins Lake

Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
Uptown
United States
Michael S.
£244
includes taxes & fees
5 Oct - 6 Oct
Artistic Loft Rooftop | 13 mins DT | 4 mins Lake
A rooftop terrace with a brick wall, large windows, and a metal railing.
A beach with a sandy shore and calm sea.
A modern kitchen with white cabinets, a built-in oven, a coffee machine, and a sink.
A modern kitchen with a dining area, a dishwasher, a coffee maker, and a view of a cityscape through a large window.

7. Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake

Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
Uptown
United States
Ashly B.
£211
includes taxes & fees
5 Oct - 6 Oct
Regal Stylish Loft Rooftop|13 mins DT |4 mins Lake
A spacious hotel lobby with a central fountain, elegant chandeliers, and a high ceiling with skylights.
A spacious living room with a view of the ocean, a chandelier, and a traditional red cabinet.
A coastal cityscape with a beach, high-rise buildings, and lush greenery.
A luxurious lobby with a central fountain, seating areas, and a high ceiling with skylights.

8. The Drake

The Drake
Downtown Chicago
United States
Carrie
£154
includes taxes & fees
1 Nov - 2 Nov
The Drake
Lake
A hotel lobby with sofas, a reception desk, a staircase, and a view of the outside.
An outdoor seating area with modern furniture, surrounded by tall buildings.
A modern living room with a sofa, a round coffee table, and a dining area with a table and chairs.

9. Kasa Lake Shore Chicago

Kasa Lake Shore Chicago
Downtown Chicago
United States
Mary
£215
includes taxes & fees
1 Nov - 2 Nov
Kasa Lake Shore Chicago
A modern living room with a fireplace, a flat-screen TV, a sofa, and a dining area.
A wooden deck with a staircase leading to an upper level, featuring a railing and two chairs.
A dining area with a wooden table and chairs, a chandelier, and a painting on the wall.
A building with a brick facade and a large glass window. There is a staircase with a black railing leading to the entrance.

10. Chic Urban Retreat Near Wrigley Field w/Parking

Chic Urban Retreat Near Wrigley Field w/Parking
Lakeview
United States
Ryan G.
£190
includes taxes & fees
13 Oct - 14 Oct
Chic Urban Retreat Near Wrigley Field w/Parking
View all properties

Top South Side Hotel Reviews

Chicago Lake Shore Hotel

Chicago Lake Shore Hotel

10/10 Excellent
"Everything was clean they are busy updating this hotel. I like to location close to the hospital and free parking."
David 2-night trip
Posted 1 day ago
Chicago Lake Shore Hotel

Explore a world of travel with Expedia