Cheap Holidays to The Loop
- Top deals for trips to The Loop
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top deals for trips to The Loop
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
2 Feb - 8 Feb
6 night stay
Geneva (GVA) to Chicago (ORD)
KLM • Direct return • Coach
Price was CHF 885, price is now CHF 600 per person
CHF 600
per person
found 19 hours ago
Our customers tell us that they can't get enough of the helpful staff at Hilton Grand Vacations Club Chicago Magnificent Mile. 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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
2 Feb - 8 Feb
6 night stay
Geneva (GVA) to Chicago (ORD)
KLM • Direct return • Coach
Save 100% on your flight
Price was CHF 1'783, price is now CHF 1'109 per person
CHF 1'109
per person
found 19 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
Level Chicago – Old Town
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'249, price is now CHF 816 per person
CHF 816
per person
found 2 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 State Street. Enjoy features like free WiFi in public areas, plus a 24-hour gym and a coffee shop/cafe. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
5.0-star property
The Peninsula Chicago
Downtown Chicago
2 Feb - 8 Feb
6 night stay
Geneva (GVA) to Chicago (ORD)
KLM • Direct return • Coach
Save 100% on your flight
Price was CHF 1'867, price is now CHF 1'295 per person
CHF 1'295
per person
found 19 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
Hotel Riu Plaza Chicago
Downtown Chicago
2 Feb - 8 Feb
6 night stay
Geneva (GVA) to Chicago (ORD)
KLM • Direct return • Coach
Price was CHF 883, price is now CHF 619 per person
CHF 619
per person
found 19 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.
The Loop Holiday Packages for 3 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
15 Feb - 18 Feb
3 night stay
Zürich (ZRH) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was CHF 775, price is now CHF 657 per person
CHF 657
per person
found 2 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.
4.0-star property
Hilton Chicago O'Hare Airport
O'Hare
15 Feb - 18 Feb
3 night stay
Zürich (ZRH) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was CHF 959, price is now CHF 835 per person
CHF 835
per person
found 2 hours ago
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 Allstate Arena. Free WiFi in public areas, a free round-trip airport shuttle and 2 restaurants are available.
4.5-star property
Pendry Chicago
Downtown Chicago
15 Feb - 18 Feb
3 night stay
Zürich (ZRH) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was CHF 808, price is now CHF 706 per person
CHF 706
per person
found 2 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.
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
15 Feb - 18 Feb
3 night stay
Zürich (ZRH) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was CHF 804, price is now CHF 711 per person
CHF 711
per person
found 2 hours ago
Our customers tell us that they can't get enough of the helpful staff at theWit Chicago, a Hilton Hotel. During your stay, you're just a quick walk from Michigan Avenue. Features include 2 bars, a full-service spa and a restaurant.
4.0-star property
The Emily Hotel
Downtown Chicago
15 Feb - 18 Feb
3 night stay
Zürich (ZRH) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was CHF 848, price is now CHF 752 per person
CHF 752
per person
found 2 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.
The Loop Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
2 Feb - 8 Feb
6 night stay
Geneva (GVA) to Chicago (ORD)
KLM • Direct return • Coach
Price was CHF 885, price is now CHF 600 per person
CHF 600
per person
found 19 hours ago
Our customers tell us that they can't get enough of the helpful staff at Hilton Grand Vacations Club Chicago Magnificent Mile. 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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
2 Feb - 8 Feb
6 night stay
Geneva (GVA) to Chicago (ORD)
KLM • Direct return • Coach
Save 100% on your flight
Price was CHF 1'783, price is now CHF 1'109 per person
CHF 1'109
per person
found 19 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
Level Chicago – Old Town
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Zürich (ZRH) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was CHF 1'249, price is now CHF 816 per person
CHF 816
per person
found 2 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 State Street. Enjoy features like free WiFi in public areas, plus a 24-hour gym and a coffee shop/cafe. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
5.0-star property
The Peninsula Chicago
Downtown Chicago
2 Feb - 8 Feb
6 night stay
Geneva (GVA) to Chicago (ORD)
KLM • Direct return • Coach
Save 100% on your flight
Price was CHF 1'867, price is now CHF 1'295 per person
CHF 1'295
per person
found 19 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
Hotel Riu Plaza Chicago
Downtown Chicago
2 Feb - 8 Feb
6 night stay
Geneva (GVA) to Chicago (ORD)
KLM • Direct return • Coach
Price was CHF 883, price is now CHF 619 per person
CHF 619
per person
found 19 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.
Best The Loop hotel deals for your holiday
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
The price is CHF 141 per night
CHF 141
5 Jan - 6 Jan 2026
includes taxes & fees
0.36 km from The Loop
Our customers tell us they can't get enough of Palmer House a Hilton Hotel's great location. During your stay, you're just a quick walk from Millennium Park. You'll find features such as a full-service spa, an indoor pool and a restaurant.
Hilton Chicago
720 S Michigan Ave Chicago IL
The price is CHF 136 per night
CHF 136
5 Jan - 6 Jan 2026
includes taxes & fees
1.29 km from The 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.
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
The price is CHF 76 per night
CHF 76
12 Jan - 13 Jan 2026
includes taxes & fees
0.52 km from The Loop
Our customers tell us that they can't get enough of the helpful staff at Club Quarters Hotel Wacker at Michigan, Chicago. During your stay, you're just a quick walk from Chicago Riverwalk. You'll find features such as free WiFi in public areas, plus a restaurant and a gym. This property offers pet-friendly amenities, such as food and water bowls.
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
0.31 km from The Loop
Our customers tell us that they can't get enough of the comfortable beds at Silversmith Hotel Chicago Downtown. 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 24-hour gym and a bar.
Pendry Chicago
230 North Michigan Avenue Chicago IL
The price is CHF 181 per night
CHF 181
12 Jan - 13 Jan 2026
includes taxes & fees
0.48 km from The Loop
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.
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
The price is CHF 156 per night
CHF 156
20 Jan - 21 Jan 2026
includes taxes & fees
0.71 km from The Loop
Our customers tell us they can't get enough of Hyatt Regency Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 4 restaurants and 2 bars.
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 The Loop
Prices found within past 7 days. 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.