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.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
8 May - 12 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
per person
found 16 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.
4.0-star property
The Emily Hotel
Downtown Chicago
15 May - 19 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
Save 100% on your flight
per person
found 17 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
Virgin Hotels Chicago
Downtown Chicago
15 May - 19 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
Save 100% on your flight
per person
found 17 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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
15 May - 19 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
Save 100% on your flight
per person
found 17 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.
5.0-star property
Park Hyatt Chicago
Downtown Chicago
15 May - 19 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
Save 100% on your flight
per person
found 17 hours 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.
Chicago Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
8 May - 12 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
per person
found 16 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.
4.0-star property
The Emily Hotel
Downtown Chicago
15 May - 19 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
Save 100% on your flight
per person
found 17 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
Virgin Hotels Chicago
Downtown Chicago
15 May - 19 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
Save 100% on your flight
per person
found 17 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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
15 May - 19 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
Save 100% on your flight
per person
found 17 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.
5.0-star property
Park Hyatt Chicago
Downtown Chicago
15 May - 19 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
Save 100% on your flight
per person
found 17 hours 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.
More Chicago hotels
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €150 per night
€150
includes taxes & fees
20 Apr - 21 Apr
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
Swissotel - Chicago
323 E Wacker Dr, Chicago, IL
The price is €211 per night
€211
includes taxes & fees
13 Apr - 14 Apr
1 km from city centre
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
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
The price is €99 per night
€99
includes taxes & fees
20 Apr - 21 Apr
1.57 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Crowne Plaza Chicago West Loop by IHG. During your stay, you're just a quick walk from University of Illinois Chicago. Features include free WiFi in public areas, plus a restaurant and a gym.
Pet-friendly
Free WiFi
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is €127 per night
€127
includes taxes & fees
21 Apr - 22 Apr
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 an indoor pool and a gym.
Pool
Pet-friendly
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €115 per night
€115
includes taxes & fees
15 Apr - 16 Apr
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
River Hotel
75 East Wacker Drive, Chicago, IL
The price is €112 per night
€112
includes taxes & fees
21 Apr - 22 Apr
0.81 km from city centre
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
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 Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
JFK
New York
ORD
Chicago
€143 Return, found 3 days ago
€143
Return
found 3 days ago
LGA
New York
ORD
Chicago
€143 Return, found 3 days ago
€143
Return
found 3 days ago
ATL
Atlanta
MDW
Chicago
€149 Return, found 3 days ago
€149
Return
found 3 days ago
Chicago neighborhoods
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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.