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

4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • 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.

4.5-star property
Pendry Chicago
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • Coach
per person
found 1 day ago
Our customers tell us they can't get enough of Pendry Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • 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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • Coach
per person
found 1 day ago
The shopping around Sable at Navy Pier Chicago, Curio Collection by Hilton gets high marks from our customers. During your stay, you'll be connected to the convention centre and just a quick walk from Lake Michigan. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.

4.0-star property
Arlo Chicago
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • Coach
per person
found 1 day ago
The sightseeing around Arlo Chicago 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 restaurant and a gym.
South Loop Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • 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.

4.5-star property
Pendry Chicago
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • Coach
per person
found 1 day ago
Our customers tell us they can't get enough of Pendry Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.

4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • 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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • Coach
per person
found 1 day ago
The shopping around Sable at Navy Pier Chicago, Curio Collection by Hilton gets high marks from our customers. During your stay, you'll be connected to the convention centre and just a quick walk from Lake Michigan. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.

4.0-star property
Arlo Chicago
Downtown Chicago
2 Oct - 6 Oct
4 night stay
Helsinki (HEL) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Helsinki (HEL)
United • Direct • Coach
per person
found 1 day ago
The sightseeing around Arlo Chicago 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 restaurant and a gym.
Best South Loop hotel deals for your holiday

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €138 per night
€138
1 Sept - 2 Sept
includes taxes & fees
1.5 km from South Loop
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 Millennium Park. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Ilmainen Wi-Fi
Ravintola

Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
The price is €110 per night
€110
25 Aug - 26 Aug
includes taxes & fees
1.41 km from South Loop
Our customers tell us that they can't get enough of the comfortable beds at Travelodge by Wyndham Downtown Chicago. During your stay, you're just a quick walk from State Street. You'll find features such as free WiFi in public areas, plus a restaurant and a coffee shop/cafe.
Ilmainen Wi-Fi
Ravintola

Hilton Chicago
720 S Michigan Ave, Chicago, IL
The price is €206 per night
€206
17 Aug - 18 Aug
includes taxes & fees
1.2 km from South Loop
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 State Street. Features include free WiFi in public areas, plus 2 restaurants and an indoor pool.
Uima-allas
Poreallas

Best Western Grant Park Hotel
1100 S Michigan Ave, Chicago, IL
The price is €127 per night
€127
24 Aug - 25 Aug
includes taxes & fees
0.85 km from South Loop
Our customers tell us that they can't get enough of the helpful staff at Best Western Grant Park Hotel. During your stay, you're just a quick walk from State Street. Enjoy features like free WiFi in public areas, plus a restaurant and a 24-hour gym.
Ilmainen Wi-Fi
Ravintola

Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street, Chicago, IL
The price is €152 per night
€152
26 Aug - 27 Aug
includes taxes & fees
0.82 km from South Loop
Hilton Garden Inn Chicago Downtown South Loop's great location gets high marks from our customers. During your stay, you're just a quick walk from State Street. Enjoy features like free WiFi in public areas, plus a restaurant and a 24-hour gym.
Uima-allas
Lemmikkiystävällinen

Sentral Michigan Avenue
808 SOUTH MICHIGAN AVENUE, Chicago, IL
The price is €208 per night
€208
4 Aug - 5 Aug
includes taxes & fees
1.1 km from South Loop
Our customers tell us they can't get enough of Sentral Michigan Avenue's great location. During your stay, you're just a quick walk from State Street. Features include free WiFi in public areas, plus an indoor pool and a restaurant. This upmarket aparthotel has 92 apartments over 50 floors. Each apartment offers a kitchen and a washer/dryer.
Uima-allas
Keittiö
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.
Cheap flights to South Loop
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LAX
Los Angeles
MDW
Chicago
€185 Return, found 4 days ago
€185
Return
found 4 days ago
LAX
Los Angeles
ORD
Chicago
€185 Return, found 4 days ago
€185
Return
found 4 days ago
LAX
Los Angeles
ORD
Chicago
€245 Return, found 4 days ago
€245
Return
found 4 days 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.