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
Fairmont Chicago at Millennium Park
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,367, price is now €1,051 per person
€1,051
per person
found 4 hours ago
Our customers tell us that they can't get enough of the sightseeing around Fairmont Chicago at Millennium Park. 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 bars and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,892, price is now €1,374 per person
€1,374
per person
found 4 hours ago
During your stay at Level Chicago Fulton Market, you're just a quick walk from Milwaukee Avenue. Free WiFi in public areas, a business centre and concierge services are available. This property offers pet-friendly amenities, such as an off-lead area.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,938, price is now €1,544 per person
€1,544
per person
found 4 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
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,334, price is now €1,071 per person
€1,071
per person
found 4 hours ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.
4.5-star property
Swissotel - Chicago
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,757, price is now €1,415 per person
€1,415
per person
found 4 hours ago
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.
Chicago Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,367, price is now €1,051 per person
€1,051
per person
found 4 hours ago
Our customers tell us that they can't get enough of the sightseeing around Fairmont Chicago at Millennium Park. 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 bars and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.
4.0-star property
Level Chicago Fulton Market
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,892, price is now €1,374 per person
€1,374
per person
found 4 hours ago
During your stay at Level Chicago Fulton Market, you're just a quick walk from Milwaukee Avenue. Free WiFi in public areas, a business centre and concierge services are available. This property offers pet-friendly amenities, such as an off-lead area.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,938, price is now €1,544 per person
€1,544
per person
found 4 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
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,334, price is now €1,071 per person
€1,071
per person
found 4 hours ago
Our customers tell us that they can't get enough of the comfortable beds at LondonHouse Chicago, Curio Collection by Hilton. During your stay, you're just a quick walk from Chicago Riverwalk. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.
4.5-star property
Swissotel - Chicago
Downtown Chicago
21 May - 25 May
4 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Return • Coach
Price was €1,757, price is now €1,415 per person
€1,415
per person
found 4 hours ago
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.
More Chicago hotels
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
The price is €123 per night
€123
26 Apr - 27 Apr
includes taxes & fees
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 €120 per night
€120
26 Apr - 27 Apr
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 an indoor pool and a gym.
Pool
Pet-friendly
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is €139 per night
€139
26 Apr - 27 Apr
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
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
The price is €147 per night
€147
27 Apr - 28 Apr
includes taxes & fees
1.47 km from city centre
During your stay at Hotel Riu Plaza Chicago, you're just a quick walk from Michigan Avenue. Enjoy features like free breakfast and free WiFi in public areas, plus 2 bars.
Breakfast included
Free WiFi
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
The price is €204 per night
€204
9 May - 10 May
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
The Wade
644 N Lake Shore Dr Chicago IL
The price is €169 per night
€169
26 Apr - 27 Apr
includes taxes & fees
1.8 km from city centre
Our customers tell us they can't get enough of The Wade's great location. During your stay, you're just a quick walk from Lake Michigan. Free WiFi in public areas, an indoor pool and a restaurant are available.
Pool
Pet-friendly
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
€161 Return, found 1 day ago
€161
Return
found 1 day ago
JFK
New York
ORD
Chicago
€170 Return, found 1 day ago
€170
Return
found 1 day ago
EWR
New York
ORD
Chicago
€187 Return, found 3 days ago
€187
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.