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

4.0-star property
Hotel Saint Clair- Magnificent Mile
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours ago
Our customers tell us they can't get enough of Hotel Saint Clair- Magnificent Mile's great location. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus a restaurant and a 24-hour gym.

4.0-star property
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours ago
Our customers tell us they can't get enough of The Allegro Royal Sonesta Hotel Chicago Loop's great location. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a 24-hour gym, a bar and breakfast (surcharge). This property offers pet-friendly amenities, such as food and water bowls.

3.5-star property
The Buckingham Hotel
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours ago
The Buckingham Hotel's great location gets high marks from our customers. During your stay, you're just a quick walk from Willis Tower. Features include a coffee shop/cafe, a snack bar/deli and a 24-hour business centre.

3.0-star property
Aloft Chicago Mag Mile
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours ago
Our customers tell us they can't get enough of Aloft Chicago Mag Mile's great location. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as free WiFi in public areas, plus an indoor pool and a restaurant.

4.0-star property
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours ago
Our customers tell us they can't get enough of Staypineapple, An Iconic Hotel, The Loop's great location. During your stay, you're just a quick walk from Michigan Avenue. A restaurant, a gym and a bar are available. This property offers pet-friendly amenities, such as food and water bowls.
South Chicago Holiday Packages for 3 Nights
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Level Chicago – Old Town
Downtown Chicago
3 Jun - 6 Jun
3 night stay
Zürich (ZRH) to Chicago (ORD)
Swiss International Air Lines • Coach
Chicago (ORD) to Zürich (ZRH)
Brussels Airlines • Coach
per person
found 1 day ago
Level Chicago – Old Town's great location gets high marks from our customers. During your stay, you're just a quick walk from Oak Street. Enjoy features like free WiFi in public areas, plus a full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
3 Jun - 6 Jun
3 night stay
Zürich (ZRH) to Chicago (ORD)
Swiss International Air Lines • Coach
Chicago (ORD) to Zürich (ZRH)
Brussels Airlines • Coach
per person
found 1 day ago
Trump International Hotel & Tower Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Free WiFi in public areas, a full-service spa and an indoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
3 Jun - 6 Jun
3 night stay
Zürich (ZRH) to Chicago (ORD)
Swiss International Air Lines • Coach
Chicago (ORD) to Zürich (ZRH)
Brussels Airlines • 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.

4.0-star property
The Emily Hotel
Downtown Chicago
3 Jun - 6 Jun
3 night stay
Zürich (ZRH) to Chicago (ORD)
Swiss International Air Lines • Coach
Chicago (ORD) to Zürich (ZRH)
Brussels Airlines • Coach
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you're just a quick walk from Milwaukee Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.

4.5-star property
Swissotel - Chicago
Downtown Chicago
3 Jun - 6 Jun
3 night stay
Zürich (ZRH) to Chicago (ORD)
Swiss International Air Lines • Coach
Chicago (ORD) to Zürich (ZRH)
Brussels Airlines • Coach
per person
found 1 day ago
The sightseeing around Swissotel - Chicago gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as 2 bars, a restaurant and a 24-hour gym.
South Chicago Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.

3.5-star property
Congress Plaza Hotel
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours ago
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.

4.0-star property
Level Chicago – Old Town
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours ago
Level Chicago – Old Town's great location gets high marks from our customers. During your stay, you're just a quick walk from Oak Street. Enjoy features like free WiFi in public areas, plus a full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.

4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours 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.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours ago
Trump International Hotel & Tower Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Free WiFi in public areas, a full-service spa and an indoor pool are available. This property offers pet-friendly amenities, such as food and water bowls.

4.0-star property
The Emily Hotel
Downtown Chicago
10 Jun - 17 Jun
7 night stay
Zürich (ZRH) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
United • Direct • Coach
per person
found 16 hours ago
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you're just a quick walk from Milwaukee Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.
Best South Chicago hotel deals for your holiday

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is CHF 159 per night
CHF 159
includes taxes & fees
1 May - 2 May
17.93 km from South Chicago
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.

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is CHF 138 per night
CHF 138
includes taxes & fees
1 May - 2 May
15.99 km from South Chicago
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 CHF 155 per night
CHF 155
includes taxes & fees
11 May - 12 May
18.51 km from South Chicago
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.

Swissotel - Chicago
323 E Wacker Dr, Chicago, IL
The price is CHF 193 per night
CHF 193
includes taxes & fees
2 May - 3 May
17.1 km from South Chicago
The sightseeing around Swissotel - Chicago gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as 2 bars, a restaurant and a 24-hour gym.

River Hotel
75 East Wacker Drive, Chicago, IL
The price is CHF 115 per night
CHF 115
includes taxes & fees
26 May - 27 May
17.35 km from South Chicago
Our customers tell us that they can't get enough of the helpful staff at River Hotel. 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. This property offers pet-friendly amenities, such as food and water bowls.

The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
The price is CHF 190 per night
CHF 190
includes taxes & fees
11 May - 12 May
17.22 km from South Chicago
Our customers tell us they can't get enough of The Allegro Royal Sonesta Hotel Chicago Loop's great location. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a 24-hour gym, a bar and breakfast (surcharge). This property offers pet-friendly amenities, such as food and water bowls.
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 Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LAX
Los Angeles
ORD
Chicago
CHF 356 Return, found 6 days ago
CHF 356
Return
found 6 days ago
FCO
Rome
ORD
Chicago
CHF 540 Return, found 5 days ago
CHF 540
Return
found 5 days ago
FCO
Rome
ORD
Chicago
CHF 546 Return, found 5 days ago
CHF 546
Return
found 5 days ago
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^Savings based on all package bookings with Flight + Hotel made on ebookers.ch 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.