An aerial view of a circular plaza with a central monument, surrounding pathways, and a waterfront.

Near South Side Hotel Guide - Adventure Sport Hotels in Near South Side, Chicago

  • 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 availability on Near South Side Adventure Sport Hotels

Our top choices for Near South Side adventure hotels

A grand lobby with a central bar, high ceilings, and classical architecture.

1. THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
4.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (1,008 reviews)
"Great stay right in the Loop and convenient to the L."
United States
Scott
The price is €173
includes taxes & fees
7 Sept - 8 Sept
THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel
An outdoor dining area with tables and umbrellas, overlooking a river with a bridge and high-rise buildings in the background.

2. Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG
3.0 star property
Downtown Chicago
8.8 out of 10, Excellent, (2,534 reviews)
"Amazing location great value will definitely come back here"
United States
Victor
The price is €219
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Chicago Dwtn - The Mart by IHG
A modern bar area with a marble countertop, leather bar stools, a chandelier, and a wall-mounted TV.

3. Ivy Boutique Hotel

Ivy Boutique Hotel
4.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (1,442 reviews)
"Very nice hotel, friendly staff."
United States
Jerry
The price is €136
includes taxes & fees
7 Sept - 8 Sept
Ivy Boutique Hotel
A woman descending a set of outdoor stairs in an urban area with tall buildings in the background.

4. voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3,779 reviews)
"Always stay here when in Chicago. Great location and great breakfast!"
United States
Leeshay
The price is €229
includes taxes & fees
7 Sept - 8 Sept
voco Chicago Downtown - Riverwalk by IHG
A historic building with a prominent casino sign, surrounded by modern skyscrapers.

5. Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile
4.0 star property
Downtown Chicago
8.2 out of 10, Very good, (3,034 reviews)
"Great location and pleasant staff."
United States
DeWayne
The price is €144
includes taxes & fees
7 Sept - 8 Sept
Hotel Felix River North/Magnificent Mile
A modern restaurant with high ceilings, exposed beams, and large windows. Tables are set with blue napkins and pink glassware.

6. The Hoxton, Chicago

The Hoxton, Chicago
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,007 reviews)
"Great stay!"
United States
Jordan
The price is €290
includes taxes & fees
7 Sept - 8 Sept
The Hoxton, Chicago
A modern living room with a large window, a flat-screen TV, and a sofa.

7. Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.2 out of 10, Wonderful, (7 reviews)
"Great location, plenty of space and clean home. "
United States
Brittany T.
The price is €476
includes taxes & fees
8 Sept - 9 Sept
Modern West Loop Gem-City Views & Prime Location 5
A modern reception area with a marble reception desk, a sofa, armchairs, and a coffee table.

8. JW Marriott Chicago

JW Marriott Chicago
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,007 reviews)
"I absolutely loved this hotel! The location was convenient, the staff was amazing and the room was comfortable. I would definitely stay here again!"
United States
Patricia
The price is €422
includes taxes & fees
10 Sept - 11 Sept
JW Marriott Chicago
A hallway with wooden flooring, a dining area with a table and chairs, and a blue sofa.

9. Villa Dubois Guest House

Villa Dubois Guest House
2.0 star property
Bronzeville
7.6 out of 10, Good, (131 reviews)
"Great place to stay. Quiet, clean and tastefully furnished. Good location for Southside destinations and good access to public transportation."
United States
Robert
The price is €124
includes taxes & fees
8 Sept - 9 Sept
Villa Dubois Guest House
A person relaxing on a sofa with a laptop, a glass of red wine, and a small table with a vase of flowers and a telephone.

10. L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (4,737 reviews)
"Great location, friendly staff."
United States
Jeff
The price is €264
includes taxes & fees
27 Sept - 28 Sept
L7 Chicago by LOTTE
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.
View all properties

Top Near South Side Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"The hotel is in a great location. All major bus and train routes are within two blocks. Rooms are good, area is safe and I would stay again."
Sue 3-night trip
Posted 3 hours ago
Congress Plaza Hotel

Frequently asked questions

Why book your hotel for couples in Near South Side with Expedia?
Expedia has some excellent hotels for couples, so get ready to spoil yourselves in Near South Side. If you have a certain budget, click on how much you want to spend and the star rating of your hotel. Whatever your trip looks like, we'll help you find a property that'll make both your sweetheart and wallet smile!
How can I find cheap hotels for couples in Near South Side?
With Expedia's user-friendly filter tool, scoring cheap hotels for couples in Near South Side is easy. To find properties that'll make your pocket and partner smile, tailor your search results by amenities, budget and star rating.

Explore a world of travel with Expedia