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 Felix River North/Magnificent Mile
Downtown Chicago
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
Our customers tell us that they can't get enough of the helpful staff at Hotel Felix River North/Magnificent Mile. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a 24-hour gym and a bar.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
Our customers tell us that they can't get enough of the helpful staff at Trump International Hotel & Tower Chicago. 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
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
Our customers tell us that they can't get enough of the helpful staff at Level Chicago – Old Town. 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 60 apartments. Each apartment offers free WiFi and a kitchen.
4.5-star property
Pendry Chicago
Downtown Chicago
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
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.
4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
Our customers tell us that they can't get enough of the comfortable beds at The Royal Sonesta Chicago River North. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus an indoor pool and a restaurant. 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.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
Our customers tell us that they can't get enough of the helpful staff at Hotel Felix River North/Magnificent Mile. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a 24-hour gym and a bar.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
Our customers tell us that they can't get enough of the helpful staff at Trump International Hotel & Tower Chicago. 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
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
Our customers tell us that they can't get enough of the helpful staff at Level Chicago – Old Town. 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 60 apartments. Each apartment offers free WiFi and a kitchen.
4.5-star property
Pendry Chicago
Downtown Chicago
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
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.
4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
28 Jun - 3 Jul
5 night stay
Dublin (DUB) to Chicago (ORD)
United • Direct return • Coach
per person
just found
Our customers tell us that they can't get enough of the comfortable beds at The Royal Sonesta Chicago River North. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus an indoor pool and a restaurant. This property offers pet-friendly amenities, such as food and water bowls.
Chicago Holidays
Can't stop daydreaming about Chicago? From flights to room nights, car hire to tours, the committed team at ebookers are the ultimate travel whisperers.
With over 500 partner airlines and more than 500,000 worldwide properties, it's never been easier to escape.
Remember, if you book a Flight + Hotel package with ebookers and see a better deal elsewhere within 48 hours pre check in, we'll match it and repay the difference. That's our Price Guarantee.
Now is the time to start ticking off your lifetime travel dreams. Whether it's a freezing mountain peak or a scorching desert, we'll help you satisfy each and every last wanderlust. Terms and Conditions apply.
More Chicago hotels
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €179 per night
€179
per night
27 May - 28 May
0.69 km from city centre
Our customers tell us they enjoy Congress Plaza Hotel's good 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.
Breakfast available
Parking available
River Hotel
75 East Wacker Drive, Chicago, IL
The price is €174 per night
€174
per night
27 May - 28 May
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
Parking available
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
The price is €136 per night
€136
per night
27 May - 28 May
1.61 km from city centre
Our customers tell us that they enjoy the shopping around Warwick Allerton - Chicago. During your stay, you'll be connected to a shopping centre and just a quick walk from Michigan Avenue. Enjoy features like a 24-hour gym, a bar and a 24-hour business centre.
Pet-friendly
Parking available
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
The price is €195 per night
€195
per night
28 May - 29 May
1.49 km from city centre
Eurostars Magnificent Mile's central 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 a gym are available.
Spa
Parking available
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €162 per night
€162
per night
27 May - 28 May
1.33 km from city centre
The free breakfast at Embassy Suites by Hilton Chicago Downtown River North gets good 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.
Pet-friendly
Pool
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
The price is €133 per night
€133
per night
27 May - 28 May
1.59 km from city centre
Our customers tell us that they can't get enough of the helpful staff at Hotel Felix River North/Magnificent Mile. During your stay, you're just a quick walk from Michigan Avenue. Features include free WiFi in public areas, plus a 24-hour gym and a bar.
Pet-friendly
Parking available
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
€118 Return, found 4 days ago
€118
Return
found 4 days ago
LGA
New York
ORD
Chicago
€137 Return, found 2 days ago
€137
Return
found 2 days ago
EWR
Newark
ORD
Chicago
€156 Return, found 3 days ago
€156
Return
found 3 days ago
Chicago neighborhoods
Other holiday destinations
Plan your trip to Chicago
Top Trending
Hotels
Flights
Packages
^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.
e1f2c88a-5b9e-479c-b4cd-5750e06fb47857404ed7-4dfd-48b6-9119-bfdc42c3b0d4