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.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
18 Dec - 22 Dec
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €869, price is now €692 per person
€692
per person
found 1 day 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.
4.5-star property
Pendry Chicago
Downtown Chicago
18 Dec - 22 Dec
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €990, price is now €745 per person
€745
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.
5.0-star property
Park Hyatt Chicago
Downtown Chicago
29 Dec - 2 Jan
4 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Coach
Chicago (ORD) to Dublin (DUB)
Brussels Airlines • Coach
Price was €1,775, price is now €1,390 per person
€1,390
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.
4.0-star property
The Emily Hotel
Downtown Chicago
18 Dec - 22 Dec
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €977, price is now €767 per person
€767
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.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
29 Dec - 2 Jan
4 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Coach
Chicago (ORD) to Dublin (DUB)
Brussels Airlines • Coach
Price was €1,354, price is now €1,077 per person
€1,077
per person
found 1 day 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.
Chicago Holiday Packages for 4 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
18 Dec - 22 Dec
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €869, price is now €692 per person
€692
per person
found 1 day 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.
4.5-star property
Pendry Chicago
Downtown Chicago
18 Dec - 22 Dec
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €990, price is now €745 per person
€745
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.
5.0-star property
Park Hyatt Chicago
Downtown Chicago
29 Dec - 2 Jan
4 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Coach
Chicago (ORD) to Dublin (DUB)
Brussels Airlines • Coach
Price was €1,775, price is now €1,390 per person
€1,390
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.
4.0-star property
The Emily Hotel
Downtown Chicago
18 Dec - 22 Dec
4 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €977, price is now €767 per person
€767
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.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
29 Dec - 2 Jan
4 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Coach
Chicago (ORD) to Dublin (DUB)
Brussels Airlines • Coach
Price was €1,354, price is now €1,077 per person
€1,077
per person
found 1 day 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.
More Chicago hotels
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €110 per night
€110
8 Dec - 9 Dec
includes taxes & fees
1.33 km from city centre
The free breakfast at Embassy Suites by Hilton Chicago Downtown River North gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a free manager's reception, plus an indoor pool and a restaurant.
Pool
Breakfast included
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/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is €103 per night
€103
7 Dec - 8 Dec
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 €116 per night
€116
10 Nov - 11 Nov
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
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
The price is €95 per night
€95
7 Dec - 8 Dec
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
Freehand Chicago
19 East Ohio Street, Chicago, IL
The price is €97 per night
€97
18 Nov - 19 Nov
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.
