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

South Side Castle Hotels

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
In two weeks
In one month
In two months
No exact matches found, but these alternatives could be just right

Recommended hotels in South Side

1. SpringHill Suites by Marriott Chicago Chinatown

SpringHill Suites by Marriott Chicago Chinatown
3.5 star property
Chinatown
9.6 out of 10, Exceptional, (1,009 reviews)
"Nice and convenient location, with nice breakfast and friendly staff."
United States
Shouan
$98 nightly
The price is $117
Dec 7 - Dec 8
Total with taxes and fees
SpringHill Suites by Marriott Chicago Chinatown

2. 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, (1,386 reviews)
"Really enjoyed my stay. Will definitely stay there again"
United States
RENE
$123 nightly
The price is $145
Dec 11 - Dec 12
Total with taxes and fees
Holiday Inn Express Hotel & Suites Chicago-Midway Airport by IHG

3. Holiday Inn Chicago – Midway Airport S by IHG

Holiday Inn Chicago – Midway Airport S by IHG
2.5 star property
West Lawn
8.0 out of 10, Very good, (1,000 reviews)
"The staff was really kind and helpful!"
United States
Dorsy
$115 nightly
The price is $133
Dec 6 - Dec 7
Total with taxes and fees
Holiday Inn Chicago – Midway Airport S by IHG

4. Hyatt Place Chicago-South/University Medical Center

Hyatt Place Chicago-South/University Medical Center
3.0 star property
Hyde Park
8.8 out of 10, Excellent, (1,013 reviews)
"Will stay here again"
United States
RENE
$152 nightly
The price is $181
Nov 22 - Nov 23
Total with taxes and fees
Hyatt Place Chicago-South/University Medical Center

5. Best Western Inn & Suites - Midway Airport

Best Western Inn & Suites - Midway Airport
3.0 star property
Burbank
7.0 out of 10, Good, (1,004 reviews)
"Always visit this location when we’re in the city. Can’t help but love them , especially the breakfast!! Best bacon ever"
United States
William
$105 nightly
The price is $116
Dec 1 - Dec 2
Total with taxes and fees
Best Western Inn & Suites - Midway Airport

6. Sophy Hyde Park

Sophy Hyde Park
4.0 star property
Hyde Park
9.4 out of 10, Exceptional, (1,000 reviews)
"I had an amazing stay! The space is gorgeous, the room service was delicious and the staff was so friendly and helpful!"
United States
Brittany
$232 nightly
The price is $272
Dec 12 - Dec 13
Total with taxes and fees
Sophy Hyde Park

7. Chicago Marriott Midway

Chicago Marriott Midway
3.5 star property
Bedford Park
8.4 out of 10, Very good, (1,007 reviews)
"Overall great stay"
United States
Cynitha
$143 nightly
The price is $168
Nov 22 - Nov 23
Total with taxes and fees
Chicago Marriott Midway

8. Jaslin Hotel

Jaslin Hotel
3.0 star property
Chinatown
9.0 out of 10, Wonderful, (1,433 reviews)
"Great stay"
United States
Myangel
$130 nightly
The price is $155
Dec 3 - Dec 4
Total with taxes and fees
Jaslin Hotel

9. Motel 6 - Chicago, IL

Motel 6 - Chicago, IL
2.0 star property
Washington Heights
7.0 out of 10, Good, (538 reviews)
"great"
United States
Darren
$86 nightly
The price is $101
Nov 15 - Nov 16
Total with taxes and fees
Motel 6 - Chicago, IL

10. Mccormick Place Guest House

Mccormick Place Guest House
3.0 star property
Bronzeville
8.6 out of 10, Excellent, (80 reviews)
"Great parking and big living room."
United States
Jasmine
$106 nightly
The price is $125
Nov 12 - Nov 13
Total with taxes and fees
Mccormick Place Guest House

11. Carlton Inn Midway

Carlton Inn Midway
2.0 star property
Archer Heights
5.8 out of 10, (1,009 reviews)
"good location for access to the city"
United States
stephen T
$107 nightly
The price is $126
Nov 12 - Nov 13
Total with taxes and fees
Carlton Inn Midway

12. Imperial Motel Chicago I-57/I-94

Imperial Motel Chicago I-57/I-94
2.5 star property
Roseland
6.8 out of 10, (3 reviews)
"😂👍"
United States
Antyon
$85 nightly
The price is $100
Nov 12 - Nov 13
Total with taxes and fees
Imperial Motel Chicago I-57/I-94

13. Chicago Lake Shore Hotel

Chicago Lake Shore Hotel
3.0 star property
Kenwood
7.2 out of 10, Good, (1,017 reviews)
"The bath was amazing to shower in!"
United States
Britany
$143 nightly
The price is $168
Nov 24 - Nov 25
Total with taxes and fees
Chicago Lake Shore Hotel

14. Hyde Park Trendy Studio Apartment in Good Spot

Hyde Park Trendy Studio Apartment in Good Spot
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location could not be beat of looking to be near University of Chicago. Within walking distance to several restaurants, coffee, shops, and stores. Perfect for our trip!"
United States
rebecca
$144 nightly
The price is $159
Nov 16 - Nov 17
Total with taxes and fees
Hyde Park Trendy Studio Apartment in Good Spot

15. Villa Dubois Guest House

Villa Dubois Guest House
2.0 star property
Bronzeville
8.4 out of 10, Very good, (131 reviews)
"Our stay was great! The staff answered all of my questions promptly, it was easy to find and not having to pay for parking was a nice bonus."
United States
Allie
$91 nightly
The price is $107
Nov 12 - Nov 13
Total with taxes and fees
Villa Dubois Guest House

16. Hyde Park Getaway | 1BR with WiFi & Workspace

Hyde Park Getaway | 1BR with WiFi & Workspace
Hyde Park
6.0 out of 10, (1 review)
"I would characterize this property as “fine”. I only needed to stay one night for a business trip and it got the job done. Getting in/out was a little cumbersome with a lockbox to retrieve a set of keys. Hot water took quite a long time to heat up and deliver for a shower. Shower bathtub and amenities were lacking. Again, it got the job done for a night of sleep."
United States
Andrew M.
$202 nightly
The price is $217
Nov 12 - Nov 13
Total with taxes and fees
Hyde Park Getaway | 1BR with WiFi & Workspace

17. Chinatown Hotel Chicago

Chinatown Hotel Chicago
1.5 star property
Chinatown
5.6 out of 10, (1,002 reviews)
"Cheap and very close to train station. 2miles away from the city."
United States
Jonna
$83 nightly
The price is $97
Dec 12 - Dec 13
Total with taxes and fees
Chinatown Hotel Chicago

18. 1BR in Prime Hyde Park Apartment

1BR in Prime Hyde Park Apartment
Hyde Park
6.0 out of 10, (1 review)
"Location was great since we were visiting the University of Chicago and the apartment matches the pictures but there were other issues. First problem was at the building entrance, both lockboxes were empty so I had no key to enter the building. I messaged the host but had to wait for a response; luckily someone exited the building and let me in. Second problem was there was a draft in each room of the apartment and none of the radiators worked. There was a small electric heater in the closet...
United States
Rebecca
$208 nightly
The price is $224
Nov 16 - Nov 17
Total with taxes and fees
1BR in Prime Hyde Park Apartment

19. Group-Friendly 4BR Hyde Park Retreat Near UChicago

Group-Friendly 4BR Hyde Park Retreat Near UChicago
Hyde Park
7.0 out of 10, Good, (7 reviews)
"Pretty standard for a VRBO property. No frills but excellent location and great that it had 4 bedrooms for our group. "
United States
Cuoghi E.
$302 nightly
The price is $321
Nov 12 - Nov 13
Total with taxes and fees
Group-Friendly 4BR Hyde Park Retreat Near UChicago

20. Homey Vibes 1BR Apt near Lake Michigan & UChicago

Homey Vibes 1BR Apt near Lake Michigan & UChicago
Kenwood
$217 nightly
The price is $235
Dec 1 - Dec 2
Total with taxes and fees
Homey Vibes 1BR Apt near Lake Michigan & UChicago
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.
Save an average of 15% on thousands of hotels when you're signed in

Top South Side Hotel Reviews

Find out more about South Side

South Side Castles information

Number of reviews
8,107
Accommodation
0 Castles
Lowest Price
$97
Highest Price
$321

Explore a world of travel with Expedia