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Check availability on Near South Side Lakeside Hotels

Our top choices for Near South Side hotels on the lake

City view
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago
4.0 star property
Near South Side
9.2 out of 10, Wonderful, (1036)
"Great stay. Staff was wonderful."
United States
Debra
The price is 4.718.798 ₫
6.158.377 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
Hyatt Regency McCormick Place Chicago
Terrace/patio
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
4.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2269)
"Smooth check in and beautiful hotel"
United States
Monique
The price is 2.356.951 ₫
3.664.725 ₫ total
includes taxes & fees
16 Dec - 17 Dec
Sable at Navy Pier Chicago, Curio Collection by Hilton
Property amenity
The Wade

The Wade

The Wade
4.5 star property
Downtown Chicago
8.4 out of 10, Very good, (1508)
"Everything was really wonderful.. would stay again for sure!! "
United States
Alexa
The price is 2.662.562 ₫
3.125.581 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
The Wade
2 restaurants, breakfast served
The Drake

The Drake

The Drake
4.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (1357)
"Excellent staff and very nice stay. "
United States
Dwight E.
The price is 3.328.993 ₫
3.907.906 ₫ total
includes taxes & fees
8 Jan - 9 Jan 2026
The Drake
Front of property
Waldorf Astoria Chicago

Waldorf Astoria Chicago

Waldorf Astoria Chicago
5.0 star property
Downtown Chicago
9.4 out of 10, Exceptional, (1000)
"Absolutely fantastic hotel great service, you couldn’t ask for more."
United States
J Michael
The price is 10.653.480 ₫
12.506.120 ₫ total
includes taxes & fees
21 Dec - 22 Dec
Waldorf Astoria Chicago
Front of property
Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago
4.0 star property
East Chicago
8.6 out of 10, Excellent, (1000)
"Great stay in clean modern room."
United States
Douglas
The price is 4.746.336 ₫
5.632.073 ₫ total
includes taxes & fees
30 Dec - 31 Dec
Ameristar Casino Hotel East Chicago
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.
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Top Near South Side Hotel Reviews

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Frequently asked questions

Why book your lakeside hotel in Near South Side with Expedia?
Expedia can help you find the perfect lakeside hotel whatever your plans and budget. Keep it affordable and get cosy in a 3-star property close to the water, or book a luxury hotel where picturesque lake scenes are on the other side of your door. Our search filters make it simple to find a place in Near South Side that suits your needs.
How can I find cheap lakeside hotels in Near South Side?
Spend your break near the water without spending big with Expedia. To find cheap lakeside hotels in Near South Side, use our filter tool to choose your price per night budget. Have your heart set on a certain area? Our handy "neighbourhood" filter will search for accommodation in your desired part of town.