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
Virgin Hotels Chicago
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
per person
found 1 day ago
Virgin Hotels 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 a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.
4.5-star property
Pendry Chicago
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
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
Level Chicago – Old Town
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
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 full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
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 Michigan Avenue. Features include free WiFi in public areas, plus 2 restaurants and 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)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
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 Michigan Avenue. 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.
Chicago Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.
4.5-star property
Virgin Hotels Chicago
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
per person
found 1 day ago
Virgin Hotels 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 a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.
4.5-star property
Pendry Chicago
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
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
Level Chicago – Old Town
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
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 full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
4.5-star property
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
14 Mar - 20 Mar
6 night stay
Dublin (DUB) to Chicago (ORD)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
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 Michigan Avenue. Features include free WiFi in public areas, plus 2 restaurants and 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)
Iberia • Direct • Coach
Chicago (ORD) to Dublin (DUB)
American Airlines • Direct • Coach
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 Michigan Avenue. 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.
More Chicago hotels
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €106 per night
€106
includes taxes & fees
12 Jan - 13 Jan
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €112 per night
€112
includes taxes & fees
26 Jan - 27 Jan
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.
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
The price is €193 per night
€193
includes taxes & fees
31 Jan - 1 Feb
0.93 km from city centre
Our customers tell us they can't get enough of Hyatt Regency Chicago's great location. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 4 restaurants and 2 bars.
Free WiFi
Restaurant
River Hotel
75 East Wacker Drive, Chicago, IL
The price is €109 per night
€109
includes taxes & fees
22 Jan - 23 Jan
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.
Hilton Chicago
720 S Michigan Ave, Chicago, IL
The price is €169 per night
€169
includes taxes & fees
18 Jan - 19 Jan
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.
Pendry Chicago
230 North Michigan Avenue, Chicago, IL
The price is €223 per night
€223
includes taxes & fees
26 Jan - 27 Jan
0.71 km from city centre
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.
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
€113 Return, found 1 day ago
€113
Return
found 1 day ago
LGA
New York
ORD
Chicago
€114 Return, found 22 hours ago
€114
Return
found 22 hours ago
EWR
New York
ORD
Chicago
€133 Return, found 2 days ago
€133
Return
found 2 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.