Adventure Hotels in South Side from $85

Name: Best Western Grant Park Hotel
Price range: $85 total
Rating: 8

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Top South Side Adventure Hotels

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$234 total

Dec 14 - Dec 15

Total with taxes and fees

This hotel's 3 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the 24-hour business center, ...

Marriott Marquis Chicago

2121 South Prairie Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$199 nightly

$234 total

Dec 18 - Dec 19

Total with taxes and fees

This smoke-free hotel features 9 restaurants, a bar/lounge, and a 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public ...

The Wheeler Mansion

2020 South Calumet Avenue Chicago IL

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This hotel doesn't skimp on freebies - guests receive free cooked-to-order breakfast, free WiFi, and free self parking. Families will appreciate the arcade/game ...

Jaslin Hotel

261 West Cermak Rd Chicago IL

Free Cancellation

Reserve now, pay when you stay

$123 nightly

$145 total

Dec 12 - Dec 13

Total with taxes and fees

A 24-hour gym is featured at this hotel, along with free WiFi in public areas and luggage storage. Multilingual staff at the 24-hour front desk can provide around-the-clock ...

Best Western Grant Park Hotel

1100 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$72 nightly

$85 total

Jan 5 - Jan 6, 2026

Total with taxes and fees

A restaurant and a 24-hour gym are featured at this hotel. WiFi in public areas is free. Valet parking, a computer station, and dry cleaning are also ...

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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.

Looking for a hotel that matches your active lifestyle? These are the adventure hotels in South Side that your mother warned you about!

Instead of playing it safe, book a stay at one of the South Side adventure hotels near the most exciting activities to take your trip up a notch. From down and dirty in the street to wet and wild in the water, you need a hotel that can help you remove all the grit and grime after a day full of adrenaline.

That’s why sport hotels in South Side are a great fit for your lifestyle. Not only are they in an area with plenty of adventure to choose from, but they’re also the perfect place to relax and unwind after a full day of excitement.

Enjoy clean and comfortable rooms with all the amenities you’d expect of a regular hotel, with the added convenience of being close to activities that get your heart pumping. From hot showers and high-thread-count sheets to tasty room service, you’ll be able to relax as you prepare to take on the day again tomorrow.

No matter what type of (slightly) dangerous activity you’re into, make sure you book your adventure hotels in South Side with Travelocity. You’ll get the best possible deal and have even more money to spend on your trip!

South Side hotels essential information

Accommodation	468 hotels
Lowest Price	$85
Highest Price	$234
Popular hotels	Hyatt Regency McCormick Place Chicago , Best Western Grant Park Hotel, Jaslin Hotel, Marriott Marquis Chicago, The Wheeler Mansion