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 Riu Plaza Chicago
Downtown Chicago
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 855, price is now CHF 598 per person
CHF 598
per person
found 20 hours ago
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'537, price is now CHF 976 per person
CHF 976
per person
found 20 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.
5.0-star property
The Peninsula Chicago
Downtown Chicago
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'606, price is now CHF 1'131 per person
CHF 1'131
per person
found 20 hours ago
The Peninsula Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants 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
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'033, price is now CHF 735 per person
CHF 735
per person
found 20 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.
4.5-star property
Pendry Chicago
Downtown Chicago
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 903, price is now CHF 643 per person
CHF 643
per person
found 20 hours 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.
South Loop Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 855, price is now CHF 598 per person
CHF 598
per person
found 20 hours ago
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'537, price is now CHF 976 per person
CHF 976
per person
found 20 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.
5.0-star property
The Peninsula Chicago
Downtown Chicago
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'606, price is now CHF 1'131 per person
CHF 1'131
per person
found 20 hours ago
The Peninsula Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants 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
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'033, price is now CHF 735 per person
CHF 735
per person
found 20 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.
4.5-star property
Pendry Chicago
Downtown Chicago
26 Feb - 3 Mar
5 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 903, price is now CHF 643 per person
CHF 643
per person
found 20 hours 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.
Best South Loop hotel deals for your holiday
Hilton Chicago
720 S Michigan Ave Chicago IL
The price is CHF 136 per night
CHF 136
1 Jan - 2 Jan 2026
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.
Pool
Whirlpool
Homewood Suites by Hilton Chicago Downtown South Loop
59 E. 11th Street Chicago IL
The price is CHF 75 per night
CHF 75
5 Jan - 6 Jan 2026
includes taxes & fees
0.82 km from South Loop
The free breakfast at Homewood Suites by Hilton Chicago Downtown South Loop gets good marks from our customers. During your stay, you're just a quick walk from State Street. Free WiFi in public areas, a free manager's reception and a restaurant are available.
Pool
Frühstück inbegriffen
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is CHF 192 per night
CHF 192
31 Dec - 1 Jan 2026
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.
Kostenloses WLAN
Restaurant
Hilton Garden Inn Chicago Downtown South Loop
55 E 11th Street Chicago IL
The price is CHF 70 per night
CHF 70
5 Jan - 6 Jan 2026
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.
Pool
Haustierfreundlich
Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel
500 South Dearborn Street Chicago IL
The price is CHF 88 per night
CHF 88
14 Jan - 15 Jan 2026
includes taxes & fees
1.49 km from South Loop
Our customers tell us they can't get enough of Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel's great location. During your stay, you're just a quick walk from State Street. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.
Kostenloses WLAN
Restaurant
Best Western Grant Park Hotel
1100 S Michigan Ave Chicago IL
The price is CHF 67 per night
CHF 67
5 Jan - 6 Jan 2026
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.
Kostenloses WLAN
Restaurant
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.
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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.