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
The Royal Sonesta Chicago River North
Downtown Chicago
4 Oct - 10 Oct
6 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €1,428, price is now €866 per person
€866
per person
found 1 day ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North'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
The Emily Hotel
Downtown Chicago
2 Nov - 7 Nov
5 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €1,426, price is now €871 per person
€871
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.
5.0-star property
Park Hyatt Chicago
Downtown Chicago
2 Nov - 7 Nov
5 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €1,968, price is now €1,235 per person
€1,235
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Park Hyatt Chicago. During your stay, you'll be connected to a shopping centre and just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a full-service spa and an indoor pool. This property offers pet-friendly amenities, such as food and water bowls.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
5 Nov - 9 Nov
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €1,592, price is now €1,036 per person
€1,036
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
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
4 Oct - 10 Oct
6 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €1,712, price is now €1,116 per person
€1,116
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Chicago Athletic Association, a Hyatt Hotel. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and 3 bars. This property offers pet-friendly amenities, such as food and water bowls.
The Loop Holiday Packages for 3 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
31 Oct - 3 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €881, price is now €636 per person
€636
per person
found 11 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
31 Oct - 3 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €1,543, price is now €968 per person
€968
per person
found 11 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
31 Oct - 3 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €1,053, price is now €699 per person
€699
per person
found 11 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.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
31 Oct - 3 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €996, price is now €673 per person
€673
per person
found 11 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.
4.5-star property
Pendry Chicago
Downtown Chicago
31 Oct - 3 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €1,038, price is now €746 per person
€746
per person
found 11 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.
The Loop Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
The Emily Hotel
Downtown Chicago
5 Nov - 9 Nov
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €1,280, price is now €880 per person
€880
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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
5 Nov - 9 Nov
4 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €1,592, price is now €1,036 per person
€1,036
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.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
10 Oct - 14 Oct
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Save 100% on your flight
Price was €1,807, price is now €1,195 per person
€1,195
per person
found 1 day 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.
4.0-star property
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
10 Oct - 14 Oct
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Save 100% on your flight
Price was €1,713, price is now €1,140 per person
€1,140
per person
found 1 day 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.
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
10 Oct - 14 Oct
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Save 100% on your flight
Price was €2,031, price is now €1,402 per person
€1,402
per person
found 1 day ago
The shopping around Sable at Navy Pier Chicago, Curio Collection by Hilton gets high marks from our customers. During your stay, you'll be connected to the convention centre and just a quick walk from Lake Michigan. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
The Loop Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
2 Nov - 7 Nov
5 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €944, price is now €629 per person
€629
per person
found 1 day ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North'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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
2 Nov - 7 Nov
5 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €1,927, price is now €1,159 per person
€1,159
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.
4.0-star property
The Emily Hotel
Downtown Chicago
2 Nov - 7 Nov
5 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €1,426, price is now €871 per person
€871
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.
5.0-star property
Park Hyatt Chicago
Downtown Chicago
2 Nov - 7 Nov
5 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €1,968, price is now €1,235 per person
€1,235
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Park Hyatt Chicago. During your stay, you'll be connected to a shopping centre and just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a full-service spa and an indoor pool. This property offers pet-friendly amenities, such as food and water bowls.
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
2 Nov - 7 Nov
5 night stay
Dublin (DUB) to Chicago (ORD)
Icelandair • Direct return • Coach
Price was €1,173, price is now €780 per person
€780
per person
found 1 day 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.
The Loop Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
4 Oct - 10 Oct
6 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €1,428, price is now €866 per person
€866
per person
found 1 day ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North'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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
4 Oct - 10 Oct
6 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €2,454, price is now €1,425 per person
€1,425
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
Pendry Chicago
Downtown Chicago
4 Oct - 10 Oct
6 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €1,761, price is now €1,063 per person
€1,063
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
Hotel Felix River North/Magnificent Mile
Downtown Chicago
4 Oct - 10 Oct
6 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €1,387, price is now €888 per person
€888
per person
found 1 day 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.
4.5-star property
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
4 Oct - 10 Oct
6 night stay
Dublin (DUB) to Chicago (ORD)
KLM • Direct return • Coach
Price was €1,712, price is now €1,116 per person
€1,116
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Chicago Athletic Association, a Hyatt Hotel. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and 3 bars. 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 €188 per night
€188
14 Sept - 15 Sept
includes taxes & fees
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
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
The price is €195 per night
€195
4 Sept - 5 Sept
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.
Pool
Spa
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is €144 per night
€144
24 Aug - 25 Aug
includes taxes & fees
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
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
The price is €266 per night
€266
1 Sept - 2 Sept
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.
Free WiFi
Restaurant
Hilton Chicago
720 S Michigan Ave, Chicago, IL
The price is €167 per night
€167
2 Sept - 3 Sept
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.
Pool
Hot tub
The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
The price is €180 per night
€180
1 Sept - 2 Sept
includes taxes & fees
0.38 km from The Loop
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.
Pet-friendly
Air conditioning
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
€184 Return, found 4 days ago
€184
Return
found 4 days ago
LAX
Los Angeles
MDW
Chicago
€200 Return, found 4 days ago
€200
Return
found 4 days ago
LAX
Los Angeles
ORD
Chicago
€200 Return, found 4 days ago
€200
Return
found 4 days ago
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^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.