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
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • 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 restaurant, a 24-hour gym and a bar. This property offers pet-friendly amenities, such as food and water bowls.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Save 100% on your flight
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.
4.5-star property
Pendry Chicago
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • 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.
4.5-star property
W Chicago - Lakeshore
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
per person
found 1 day ago
Our customers tell us they can't get enough of W Chicago - Lakeshore's great location. During your stay, you're just a quick walk from Lake Michigan. Free WiFi in public areas, an indoor pool and a restaurant are available. This property offers pet-friendly amenities, such as food and water bowls.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • 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 full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
Downtown Chicago Holiday Packages for 6-7 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • 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 restaurant, a 24-hour gym and a bar. This property offers pet-friendly amenities, such as food and water bowls.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
Save 100% on your flight
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.
4.5-star property
Pendry Chicago
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • 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.
4.5-star property
W Chicago - Lakeshore
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • Return • Coach
per person
found 1 day ago
Our customers tell us they can't get enough of W Chicago - Lakeshore's great location. During your stay, you're just a quick walk from Lake Michigan. Free WiFi in public areas, an indoor pool and a restaurant are available. This property offers pet-friendly amenities, such as food and water bowls.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
7 Feb - 14 Feb
7 night stay
Dublin (DUB) to Chicago (ORD)
Aer Lingus • 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 full-service spa and a 24-hour gym. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
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
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is €95 per night
€95
includes taxes & fees
24 Nov - 25 Nov
1.26 km from Downtown Chicago
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
River Hotel
75 East Wacker Drive, Chicago, IL
The price is €111 per night
€111
includes taxes & fees
18 Dec - 19 Dec
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
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
The price is €184 per night
€184
includes taxes & fees
15 Dec - 16 Dec
1.54 km from Downtown Chicago
Our customers tell us they can't get enough of The Westin Michigan Avenue 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 a full-service spa and a restaurant.
Club Quarters Hotel, Central Loop, Chicago
111 West Adams Street, Chicago, IL
The price is €107 per night
€107
includes taxes & fees
18 Dec - 19 Dec
0.74 km from Downtown Chicago
Our customers tell us they can't get enough of Club Quarters Hotel, Central Loop, Chicago'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 a restaurant and a 24-hour gym. This property offers pet-friendly amenities, such as food and water bowls.
Eurostars Magnificent Mile
660 North State Street, Chicago, IL
The price is €150 per night
€150
includes taxes & fees
17 Dec - 18 Dec
0.92 km from Downtown Chicago
Eurostars Magnificent Mile'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 a gym are available.
Hotel Felix River North/Magnificent Mile
111 W Huron St, Chicago, IL
The price is €128 per night
€128
includes taxes & fees
26 Nov - 27 Nov
1.01 km from Downtown Chicago
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.
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
€206 Return, found 4 days ago
€206
Return
found 4 days ago
LAX
Los Angeles
MDW
Chicago
€250 Return, found 4 days ago
€250
Return
found 4 days ago
LAX
Los Angeles
ORD
Chicago
€250 Return, found 4 days ago
€250
Return
found 4 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.