
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
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 1 day 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.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • 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 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
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • 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 24-hour gym and a coffee shop/cafe. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.

4.5-star property
Pendry Chicago
Downtown Chicago
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • 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
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 1 day ago
Our customers tell us they can't get enough of The Allegro Royal Sonesta Hotel Chicago Loop's great location. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a 24-hour gym, a bar and breakfast (surcharge). This property offers pet-friendly amenities, such as food and water bowls.
Chicago Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.

4.5-star property
Fairmont Chicago at Millennium Park
Downtown Chicago
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 1 day 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.

5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • 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 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
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • 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 24-hour gym and a coffee shop/cafe. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.

4.5-star property
Pendry Chicago
Downtown Chicago
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • 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
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
19 Aug - 24 Aug
5 night stay
Dublin (DUB) to Chicago (ORD)
American Airlines • Direct return • Coach
per person
found 1 day ago
Our customers tell us they can't get enough of The Allegro Royal Sonesta Hotel Chicago Loop's great location. During your stay, you're just a quick walk from Michigan Avenue. You'll find features such as a 24-hour gym, a bar and breakfast (surcharge). 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 €118 per night
€118
7 Jul - 8 Jul
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 Art Institute of Chicago. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
Free WiFi
Restaurant

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
The price is €254 per night
€254
6 Jul - 7 Jul
includes taxes & fees
1.21 km from city centre
Our customers tell us they can't get enough of InterContinental Chicago Magnificent Mile by IHG's great location. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and an indoor pool.
Pool
Spa

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is €152 per night
€152
10 Jul - 11 Jul
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

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €180 per night
€180
10 Jul - 11 Jul
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

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is €134 per night
€134
7 Jul - 8 Jul
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

The Whitehall Hotel, BW Premier Collection
105 E Delaware Pl, Chicago, IL
The price is €141 per night
€141
4 Aug - 5 Aug
includes taxes & fees
2.04 km from city centre
The Whitehall Hotel, BW Premier Collection's great location gets high marks from our customers. During your stay, you're just a quick walk from Michigan Avenue. Free breakfast, free WiFi in public areas and a restaurant are available.
Breakfast included
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.
ATL
Atlanta
MDW
Chicago
€125 Return, found 6 hours ago
€125
Return
found 6 hours ago
ATL
Atlanta
ORD
Chicago
€125 Return, found 6 hours ago
€125
Return
found 6 hours ago
DFW
Dallas
ORD
Chicago
€134 Return, found 1 day ago
€134
Return
found 1 day 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.