Chicago Holidays
- Top Chicago holiday packages
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top Chicago holiday packages
Price found within the past 48 hours. Click for updated prices.
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Price was €899, price is now €705 per person
€705
per person
found 15 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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Save 100% on your flight
Price was €1,598, price is now €1,100 per person
€1,100
per person
found 15 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.
4.5-star property
Pendry Chicago
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Price was €1,103, price is now €770 per person
€770
per person
found 15 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.
4.0-star property
The Emily Hotel
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Price was €1,061, price is now €828 per person
€828
per person
found 15 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
JW Marriott Chicago
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Price was €1,021, price is now €804 per person
€804
per person
found 15 hours ago
JW Marriott Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Willis Tower. Enjoy features like a full-service spa, an indoor pool and a restaurant.
Chicago Holiday Packages for 3 Nights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Price was €899, price is now €705 per person
€705
per person
found 15 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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Save 100% on your flight
Price was €1,598, price is now €1,100 per person
€1,100
per person
found 15 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.
4.5-star property
Pendry Chicago
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Price was €1,103, price is now €770 per person
€770
per person
found 15 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.
4.0-star property
The Emily Hotel
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Price was €1,061, price is now €828 per person
€828
per person
found 15 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
JW Marriott Chicago
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Return • Coach
Price was €1,021, price is now €804 per person
€804
per person
found 15 hours ago
JW Marriott Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Willis Tower. Enjoy features like a full-service spa, an indoor pool and a restaurant.
More Chicago hotels
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
0.69 km from city centre
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
Hilton Chicago O'Hare Airport
O'Hare International Airport, Chicago, IL
The price is €215 per night
€215
18 Oct - 19 Oct
includes taxes & fees
25.24 km from city centre
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.
Free airport shuttle
Pet-friendly
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
The price is €179 per night
€179
2 Oct - 3 Oct
includes taxes & fees
1.21 km from city centre
Our customers tell us that they can't get enough of the sightseeing around Hilton Garden Inn Chicago Downtown/Magnificent Mile. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus an indoor pool and a restaurant.
Pool
Pet-friendly
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is €161 per night
€161
20 Oct - 21 Oct
includes taxes & fees
2.17 km from city centre
The shopping around Hilton Chicago/Magnificent Mile Suites gets high marks from our customers. 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 gym and a business centre.
Pet-friendly
Free WiFi
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is €181 per night
€181
28 Sept - 29 Sept
includes taxes & fees
0.73 km from city centre
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
Freehand Chicago
19 East Ohio Street, Chicago, IL
The price is €147 per night
€147
21 Oct - 22 Oct
includes taxes & fees
1.3 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Freehand Chicago. 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.
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.
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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.
