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.
4.0-star property
Hilton Orrington / Evanston
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 20 hours ago
Our customers tell us they can't get enough of Hilton Orrington / Evanston's great location. During your stay, you'll be within walking distance of Halim Time & Glass Museum. Enjoy features like 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
Virgin Hotels Chicago
Downtown Chicago
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 20 hours ago
Virgin Hotels Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Enjoy features like 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
Level Chicago – Old Town
Downtown Chicago
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 20 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 full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
3.0-star property
Dorothy's
Lakeview
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 20 hours ago
During your stay at Dorothy's, you're just a quick walk from Wrigley Field. Free breakfast, free WiFi in public areas and laundry facilities are available.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
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.
The Loop Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hilton Orrington / Evanston
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 20 hours ago
Our customers tell us they can't get enough of Hilton Orrington / Evanston's great location. During your stay, you'll be within walking distance of Halim Time & Glass Museum. Enjoy features like 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
Virgin Hotels Chicago
Downtown Chicago
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 20 hours ago
Virgin Hotels Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. Enjoy features like 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
Level Chicago – Old Town
Downtown Chicago
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 20 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 full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
3.0-star property
Dorothy's
Lakeview
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 20 hours ago
During your stay at Dorothy's, you're just a quick walk from Wrigley Field. Free breakfast, free WiFi in public areas and laundry facilities are available.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
14 Mar - 21 Mar
7 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
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.
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
The price is €118 per night
€118
includes taxes & fees
23 Dec - 24 Dec
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 Millennium Park. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Free WiFi
Restaurant
River Hotel
75 East Wacker Drive, Chicago, IL
The price is €105 per night
€105
includes taxes & fees
20 Jan - 21 Jan 2025
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
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
The price is €185 per night
€185
includes taxes & fees
10 Jan - 11 Jan 2025
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.
Free WiFi
Restaurant
Hilton Chicago
720 S Michigan Ave, Chicago, IL
The price is €162 per night
€162
includes taxes & fees
29 Dec - 30 Dec
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.
Pool
Pet-friendly
L7 Chicago by LOTTE
225 N Wabash Ave, Chicago, IL
The price is €151 per night
€151
includes taxes & fees
5 Jan - 6 Jan 2025
0.4 km from The Loop
The shopping around L7 Chicago by LOTTE gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. 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
Pendry Chicago
230 North Michigan Avenue, Chicago, IL
The price is €219 per night
€219
includes taxes & fees
4 Jan - 5 Jan 2025
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.
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
€202 Return, found 8 hours ago
€202
Return
found 8 hours ago
LAX
Los Angeles
MDW
Chicago
€245 Return, found 2 days ago
€245
Return
found 2 days ago
LAX
Los Angeles
ORD
Chicago
€288 Return, found 8 hours ago
€288
Return
found 8 hours ago
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Flights
^Savings based on all package bookings with Flight + Hotel made on ebookers.ie 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.