The Loop Holidays
- Top The Loop holiday packages
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top The Loop holiday packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Swissotel - Chicago
Downtown Chicago
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • 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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Save 100% on your flight
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.
5.0-star property
Art Villa
West Town
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Save 100% on your flight
per person
found 1 day ago
During your stay at Art Villa , you'll be within walking distance of United Center. Features include free WiFi in public areas, free self-parking and a free round-trip airport shuttle. Built in 2017, this luxury aparthotel has 5 apartments. Some of the pet-friendly amenities that this property offers include food and water bowls and an off-lead area. Each apartment offers free WiFi and rooftop hot tubs.
4.5-star property
Pendry Chicago
Downtown Chicago
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • 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.
4.0-star property
Arlo Chicago
Downtown Chicago
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • 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.
The Loop Holiday Packages for 3 Nights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Swissotel - Chicago
Downtown Chicago
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • 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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Save 100% on your flight
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.
5.0-star property
Art Villa
West Town
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Save 100% on your flight
per person
found 1 day ago
During your stay at Art Villa , you'll be within walking distance of United Center. Features include free WiFi in public areas, free self-parking and a free round-trip airport shuttle. Built in 2017, this luxury aparthotel has 5 apartments. Some of the pet-friendly amenities that this property offers include food and water bowls and an off-lead area. Each apartment offers free WiFi and rooftop hot tubs.
4.5-star property
Pendry Chicago
Downtown Chicago
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • 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.
4.0-star property
Arlo Chicago
Downtown Chicago
5 Sept - 8 Sept
3 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • 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.
The Loop Holidays
When you're finally ready to break free from the nine-to-five and discover The Loop's unique delights, ebookers will be right here to guide you to the ultimate deals on flights and accommodation.
With over 500 partner airlines and more than 500,000 properties around the world, it's easy to break-free from the everyday.
Would you like a little more peace of mind? If you find a better Flight + Package deal somewhere else within 48 hours pre check in, we guarantee we'll meet it and repay you the difference — that's our Price Guarantee.
The time is right now! Chase the wanderer within and never let go. Every destination is teeming with incredible surprises and new experiences, so let us help pull it all together.Terms and Conditions apply.
More The Loop hotels
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
1.02 km from The 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 Art Institute of Chicago. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Free WiFi
Restaurant
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
0.48 km from The Loop
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.
Free WiFi
Restaurant
Swissotel - Chicago
323 E Wacker Dr, Chicago, IL
0.86 km from The Loop
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.
Spa
Pet-friendly
River Hotel
75 East Wacker Drive, Chicago, IL
0.52 km from The Loop
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.
Pet-friendly
Free WiFi
Travelodge by Wyndham Downtown Chicago
65 E Harrison St, Chicago, IL
1.08 km from The 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 Art Institute of Chicago. You'll find features such as free WiFi in public areas, plus a restaurant and a coffee shop/cafe.
Free WiFi
Restaurant
The Royal Sonesta Chicago Downtown
71 E Wacker Dr, Chicago, IL
0.5 km from The Loop
The sightseeing around The Royal Sonesta Chicago Downtown gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. You'll find features such as a restaurant, a 24-hour gym and a bar.
Pet-friendly
Free WiFi
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.
LAX
Los Angeles
ORD
Chicago
€173 Return, found 1 day ago
€173
Return
found 1 day ago
LAX
Los Angeles
MDW
Chicago
€223 Return, found 1 day ago
€223
Return
found 1 day ago
LAX
Los Angeles
ORD
Chicago
€223 Return, found 1 day ago
€223
Return
found 1 day ago
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