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
Hotel Riu Plaza Chicago
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,434, price is now €935 per person
€935
per person
found 1 day ago
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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €2,104, price is now €1,372 per person
€1,372
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
Level Chicago – Old Town
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,578, 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.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,529, price is now €1,083 per person
€1,083
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
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,332, price is now €961 per person
€961
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.
Chicago Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
29 Jan - 2 Feb
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was €746, price is now €633 per person
€633
per person
found 1 day 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.
5.0-star property
The Peninsula Chicago
Downtown Chicago
29 Jan - 2 Feb
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was €1,644, price is now €1,315 per person
€1,315
per person
found 1 day ago
The Peninsula Chicago's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and a full-service spa. This property offers pet-friendly amenities, such as food and water bowls.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
29 Jan - 2 Feb
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was €844, price is now €689 per person
€689
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
29 Jan - 2 Feb
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was €852, price is now €697 per person
€697
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
Hilton Chicago O'Hare Airport
O'Hare
29 Jan - 2 Feb
4 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
Price was €965, price is now €792 per person
€792
per person
found 1 day ago
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.
Chicago Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Hotel Riu Plaza Chicago
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,434, price is now €935 per person
€935
per person
found 1 day ago
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.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €2,104, price is now €1,372 per person
€1,372
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
Level Chicago – Old Town
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,578, 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.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,529, price is now €1,083 per person
€1,083
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
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Price was €1,332, price is now €961 per person
€961
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.
More Chicago hotels
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
The price is €89 per night
€89
5 Jan - 6 Jan 2026
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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
The price is €152 per night
€152
3 Jan - 4 Jan 2026
includes taxes & fees
0.09 km from city centre
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
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
The price is €74 per night
€74
25 Dec - 26 Dec
includes taxes & fees
0.8 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Club Quarters Hotel Wacker at Michigan, Chicago. During your stay, you're just a quick walk from Chicago Riverwalk. You'll find features such as 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
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
0.19 km from city centre
Our customers tell us that they can't get enough of the comfortable beds at Silversmith Hotel Chicago Downtown. 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 24-hour gym and a bar.
Free WiFi
Air conditioning
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
The price is €195 per night
€195
16 Jan - 17 Jan 2026
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 Chicago
720 S Michigan Ave Chicago IL
The price is €139 per night
€139
30 Dec - 31 Dec
includes taxes & fees
0.96 km from city centre
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
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.
