Downtown Chicago Holidays
- Top Downtown Chicago holiday packages
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top Downtown 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
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
per person
found 6 hours ago
Hotel Felix River North/Magnificent Mile's great location gets high marks from our customers. 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.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
per person
found 6 hours 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.
4.0-star property
Kinzie Hotel
Downtown Chicago
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
per person
found 6 hours ago
Kinzie Hotel's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. A free manager's reception, a restaurant and a gym are available. This property offers pet-friendly amenities, such as food and water bowls.
4.0-star property
The Emily Hotel
Downtown Chicago
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
per person
found 6 hours ago
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you're just a quick walk from Milwaukee Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
Save 100% on your flight
per person
found 6 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.
Downtown 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
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
per person
found 6 hours ago
Hotel Felix River North/Magnificent Mile's great location gets high marks from our customers. 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.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
per person
found 6 hours 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.
4.0-star property
Kinzie Hotel
Downtown Chicago
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
per person
found 6 hours ago
Kinzie Hotel's great location gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. A free manager's reception, a restaurant and a gym are available. This property offers pet-friendly amenities, such as food and water bowls.
4.0-star property
The Emily Hotel
Downtown Chicago
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
per person
found 6 hours ago
Our customers tell us that they can't get enough of the helpful staff at The Emily Hotel. During your stay, you're just a quick walk from Milwaukee Avenue. Features include free WiFi in public areas, plus a restaurant and a 24-hour gym.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
20 May - 25 May
5 night stay
Dublin (DUB) to Chicago (ORD)
British Airways • Direct return • Coach
Save 100% on your flight
per person
found 6 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.
Downtown Chicago Holidays
Ready to revitalize your mind, body and spirit with some Downtown Chicago magic? The team at ebookers are experienced at making holiday fantasies into precious memories.
You want your sheets off-white and your breakfast on a rooftop? Too easy. With over 500 partner airlines and more than 500,000 worldwide properties to browse though, the world is at your feet.
Our Price Guarantee means that if you secure a Flight + Hotel package with ebookers, and then spot a better deal elsewhere within 48 hours pre check in, we'll match it and repay the difference. What's holding you back?
The time is now! Chase your inner adventurer and never let go. Every place is bursting with surprises and new things to uncover, so allow us to help you get there.Terms and Conditions apply.
More Downtown Chicago hotels
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
The price is €100 per night
€100
includes taxes & fees
6 Apr - 7 Apr
1.58 km from Downtown Chicago
Our customers tell us that they can't get enough of the helpful staff at Crowne Plaza Chicago West Loop by IHG. During your stay, you're just a quick walk from University of Illinois Chicago. Features include free WiFi in public areas, plus a restaurant and a gym.
Pet-friendly
Free WiFi
Swissotel - Chicago
323 E Wacker Dr, Chicago, IL
The price is €207 per night
€207
includes taxes & fees
4 Apr - 5 Apr
0.83 km from Downtown Chicago
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.
Spa
Pet-friendly
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €137 per night
€137
includes taxes & fees
13 Apr - 14 Apr
0.76 km from Downtown Chicago
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
River Hotel
75 East Wacker Drive, Chicago, IL
The price is €107 per night
€107
includes taxes & fees
13 Apr - 14 Apr
0.36 km from Downtown Chicago
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
Free WiFi
L7 Chicago by LOTTE
225 N Wabash Ave, Chicago, IL
The price is €182 per night
€182
includes taxes & fees
31 Mar - 1 Apr
0.28 km from Downtown Chicago
The shopping around L7 Chicago by LOTTE gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. 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.
Pet-friendly
Free WiFi
Holiday Inn Chicago Dwtn - The Mart by IHG
350 West Wolf Point Plaza, Building 2, Chicago, IL
The price is €141 per night
€141
includes taxes & fees
20 Apr - 21 Apr
0.76 km from Downtown Chicago
Our customers tell us they can't get enough of Holiday Inn Chicago Dwtn - The Mart by IHG's great location. During your stay, you're just a quick walk from Merchandise Mart. Free WiFi in public areas, 2 restaurants and an indoor pool are available.
Pool
Free WiFi
Don't see what you're looking for?
See all available properties in Downtown Chicago
View all propertiesLowest 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 Downtown Chicago
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LAX
Los Angeles
ORD
Chicago
€166 Return, found 3 days ago
€166
Return
found 3 days ago
LAX
Los Angeles
ORD
Chicago
€238 Return, found 4 days ago
€238
Return
found 4 days ago
LAX
Los Angeles
MDW
Chicago
€256 Return, found 2 days ago
€256
Return
found 2 days ago
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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.