Photo by Richard Remington

Find Adventure Hotels in South Side, IL

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Check availability on South Side Adventure Hotels

Our top choices for South Side adventure hotels

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG
2.5 star property
Bedford Park
8.8 out of 10, Excellent, (1233)
"Will definitely stay there again ."
United States
Jose Remedios
The price is NT$3,494
NT$4,104 total
includes taxes & fees
Dec 21 - Dec 22
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

Villa Dubois Guest House

Villa Dubois Guest House
2.0 star property
Bronzeville
8.6 out of 10, Excellent, (78)
"My stay was very pleasant. The accommodation was comfortable, easily accessible, and well connected to public transport. I highly recommend it to anyone visiting the area."
United States
Lizeth
The price is NT$2,340
NT$2,746 total
includes taxes & fees
Dec 14 - Dec 15
Villa Dubois Guest House

voco Chicago Downtown - Riverwalk by IHG

voco Chicago Downtown - Riverwalk by IHG
3.5 star property
Downtown Chicago
8.8 out of 10, Excellent, (3460)
"Amazing stay, beautiful view!"
United States
Joshua
The price is NT$3,288
NT$3,860 total
includes taxes & fees
Dec 14 - Dec 15
voco Chicago Downtown - Riverwalk by IHG

L7 Chicago by LOTTE

L7 Chicago by LOTTE
4.5 star property
Downtown Chicago
9.6 out of 10, Exceptional, (3357)
"I loved the location."
United States
Laura
The price is NT$4,396
NT$5,161 total
includes taxes & fees
Jan 1 - 2026/1/2
L7 Chicago by LOTTE

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, (2034)
"room was good,location was perfect!"
United States
Kyan
The price is NT$3,251
NT$3,817 total
includes taxes & fees
Dec 22 - Dec 23
Holiday Inn Chicago Dwtn - The Mart by IHG

Thompson Chicago, by Hyatt

Thompson Chicago, by Hyatt
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1295)
"Great hotel!"
United States
Julie
The price is NT$4,211
NT$5,864 total
includes taxes & fees
Dec 29 - Dec 30
Thompson Chicago, by Hyatt

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical
3.0 star property
Downtown Chicago
8.6 out of 10, Excellent, (2285)
"Excellent hotel. Loved staying there"
United States
cristina
The price is NT$3,088
NT$3,625 total
includes taxes & fees
Jan 5 - 2026/1/6
Sonesta ES Suites Chicago Downtown Magnificent Mile - Medical

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile
4.5 star property
Downtown Chicago
9.4 out of 10, Exceptional, (2257)
"The staff, food, and service were great. "
United States
Randy
The price is NT$5,025
NT$6,815 total
includes taxes & fees
Dec 17 - Dec 18
Sofitel Chicago Magnificent Mile

The Talbott, Autograph Collection

The Talbott, Autograph Collection
4.5 star property
Downtown Chicago
9.2 out of 10, Wonderful, (59)
"The location is great, always outstanding service."
United States
Yazmin
The price is NT$3,694
NT$5,254 total
includes taxes & fees
Jan 11 - 2026/1/12
The Talbott, Autograph Collection

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, (2435)
"Staff was amazing! "
United States
Erica
Hotel Felix River North/Magnificent Mile
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.

Top South Side Hotel Reviews

Explore a world of travel with Expedia