
Cheap Holidays to Near South Side
- Top deals for trips to Near South Side
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top deals for trips to Near South Side
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 1 day ago
Hotel Felix River North/Magnificent Mile's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a 24-hour gym and a bar.

4.0-star property
Level Chicago - River North
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
Save 100% on your flight
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Level Chicago - River North. During your stay, you're just a quick walk from Merchandise Mart. Enjoy features like free WiFi in public areas, plus a gym and concierge services. This property offers pet-friendly amenities, such as an off-lead area.

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 1 day ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.

4.0-star property
Hilton Chicago
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 1 day ago
Our customers tell us they can't get enough of Hilton Chicago's great location. During your stay, you're just a quick walk from Art Institute of Chicago. Features include free WiFi in public areas, plus 2 restaurants and an indoor pool.

4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 1 day ago
Our customers tell us that they can't get enough of the sightseeing around Fairmont Chicago at Millennium Park. During your stay, you're just a quick walk from Millennium Park. You'll find features such as free WiFi in public areas, plus 2 bars and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.
Near South Side Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 1 day ago
Hotel Felix River North/Magnificent Mile's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a 24-hour gym and a bar.

4.0-star property
Level Chicago - River North
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
Save 100% on your flight
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Level Chicago - River North. During your stay, you're just a quick walk from Merchandise Mart. Enjoy features like free WiFi in public areas, plus a gym and concierge services. This property offers pet-friendly amenities, such as an off-lead area.

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 1 day ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.

4.0-star property
Hilton Chicago
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 1 day ago
Our customers tell us they can't get enough of Hilton Chicago's great location. During your stay, you're just a quick walk from Art Institute of Chicago. Features include free WiFi in public areas, plus 2 restaurants and an indoor pool.

4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
20 Sept - 27 Sept
7 night stay
Helsinki (HEL) to Chicago (ORD)
KLM • Direct return • Coach
per person
found 1 day ago
Our customers tell us that they can't get enough of the sightseeing around Fairmont Chicago at Millennium Park. During your stay, you're just a quick walk from Millennium Park. You'll find features such as free WiFi in public areas, plus 2 bars and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.
Best Near South Side hotel deals for your holiday

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
The price is €254 per night
€254
7 Jul - 8 Jul
includes taxes & fees
3.77 km from Near South Side
Our customers tell us they can't get enough of InterContinental Chicago Magnificent Mile by IHG's great location. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and an indoor pool.
Uima-allas
Kylpylä

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €143 per night
€143
4 Aug - 5 Aug
includes taxes & fees
2.02 km from Near South Side
Our customers tell us they can't get enough of Congress Plaza Hotel's great location. During your stay, you're just a quick walk from Art Institute of Chicago. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is €158 per night
€158
10 Jul - 11 Jul
includes taxes & fees
4.71 km from Near South Side
The shopping around Hilton Chicago/Magnificent Mile Suites gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as free WiFi in public areas, plus a gym and a business centre.

Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
The price is €190 per night
€190
26 Jul - 27 Jul
includes taxes & fees
27.12 km from Near South Side
Our customers tell us that they can't get enough of the helpful staff at Hilton Chicago O'Hare Airport. During your stay, you'll be connected to the airport and close to Rosemont Theatre. Free WiFi in public areas, a free round-trip airport shuttle and 2 restaurants are available.

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €192 per night
€192
10 Jul - 11 Jul
includes taxes & fees
4 km from Near South Side
The free breakfast at Embassy Suites by Hilton Chicago Downtown River North gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a free manager's reception, plus an indoor pool and a restaurant.
Uima-allas
Aamiainen sisältyy hintaan

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is €135 per night
€135
7 Jul - 8 Jul
includes taxes & fees
3.32 km from Near South Side
The sightseeing around citizenM Chicago Downtown gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Free WiFi in public areas, a restaurant and a gym are available.
Ilmainen Wi-Fi
Ravintola
Don't see what you're looking for?
See all available properties in Near South Side
View all propertiesLowest 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.
Cheap flights to Near South Side
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LAX
Los Angeles
MDW
Chicago
€218 Return, found 14 hours ago
€218
Return
found 14 hours ago
LAX
Los Angeles
ORD
Chicago
€218 Return, found 14 hours ago
€218
Return
found 14 hours ago
LAX
Los Angeles
ORD
Chicago
€233 Return, found 14 hours ago
€233
Return
found 14 hours ago
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^Savings based on all package bookings with Flight + Hotel made on ebookers.fi from 2019-04-01 - 2020-03-31 as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.