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.
3.0-star property
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Swiss International Air Lines • Direct • Coach
Price was €898, price is now €706 per person
€706
per person
found 1 day ago
Our customers tell us that they can't get enough of the sightseeing around Hilton Garden Inn Chicago Downtown/Magnificent Mile. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus an indoor pool and a restaurant.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Swiss International Air Lines • Direct • Coach
Save 100% on your flight
Price was €1,559, price is now €1,040 per person
€1,040
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
30 Oct - 2 Nov
3 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
American Airlines • Coach
Price was €1,421, price is now €1,071 per person
€1,071
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
30 Oct - 2 Nov
3 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
American Airlines • Coach
Price was €1,341, price is now €1,058 per person
€1,058
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.
3.0-star property
Hilton Garden Inn Chicago Central Loop
Downtown Chicago
30 Oct - 3 Nov
4 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
British Airways • Coach
Price was €1,256, price is now €1,039 per person
€1,039
per person
found 3 hours ago
Our customers tell us they can't get enough of Hilton Garden Inn Chicago Central Loop's great location. During your stay, you're just a quick walk from Willis Tower. Features include free WiFi in public areas, plus 2 restaurants and 2 bars.
Downtown Chicago Holiday Packages for 3 Nights
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Hilton Garden Inn Chicago Downtown/Magnificent Mile
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Swiss International Air Lines • Direct • Coach
Price was €898, price is now €706 per person
€706
per person
found 1 day ago
Our customers tell us that they can't get enough of the sightseeing around Hilton Garden Inn Chicago Downtown/Magnificent Mile. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus an indoor pool and a restaurant.
5.0-star property
Trump International Hotel & Tower Chicago
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Swiss International Air Lines • Direct • Coach
Save 100% on your flight
Price was €1,559, price is now €1,040 per person
€1,040
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
30 Oct - 2 Nov
3 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
American Airlines • Coach
Price was €1,421, price is now €1,071 per person
€1,071
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
30 Oct - 2 Nov
3 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
American Airlines • Coach
Price was €1,341, price is now €1,058 per person
€1,058
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.
4.0-star property
Level Chicago - River North
Downtown Chicago
30 Oct - 2 Nov
3 night stay
Dublin (DUB) to Chicago (ORD)
Lufthansa • Direct • Coach
Chicago (ORD) to Dublin (DUB)
Swiss International Air Lines • Direct • Coach
Price was €950, price is now €751 per person
€751
per person
found 1 day ago
Our customers tell us that they can't get enough of the helpful staff at Level Chicago - River North. During your stay, you're just a quick walk from Merchandise Mart. Enjoy features like free WiFi in public areas, plus a gym and concierge services. This property offers pet-friendly amenities, such as an off-lead area.
Downtown Chicago Holiday Packages for 4 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
30 Oct - 3 Nov
4 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
British Airways • Coach
Price was €1,164, price is now €926 per person
€926
per person
found 3 hours 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.
4.5-star property
Pendry Chicago
Downtown Chicago
30 Oct - 3 Nov
4 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
British Airways • Coach
Price was €1,542, price is now €1,170 per person
€1,170
per person
found 3 hours 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
30 Oct - 3 Nov
4 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
British Airways • Coach
Price was €1,399, price is now €1,064 per person
€1,064
per person
found 3 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 24-hour gym and a coffee shop/cafe. This upmarket aparthotel has 35 apartments. Each apartment offers free WiFi and a kitchen.
4.0-star property
The Emily Hotel
Downtown Chicago
30 Oct - 3 Nov
4 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
British Airways • Coach
Price was €1,470, price is now €1,119 per person
€1,119
per person
found 3 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.
4.0-star property
Hotel Felix River North/Magnificent Mile
Downtown Chicago
30 Oct - 3 Nov
4 night stay
Shannon (SNN) to Chicago (ORD)
Aer Lingus • Coach
Chicago (ORD) to Shannon (SNN)
British Airways • Coach
Price was €1,288, price is now €1,015 per person
€1,015
per person
found 3 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.
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 €198 per night
€198
13 Sept - 14 Sept
includes taxes & fees
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is €178 per night
€178
14 Sept - 15 Sept
includes taxes & fees
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
Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
The price is €163 per night
€163
14 Sept - 15 Sept
includes taxes & fees
0.65 km from Downtown Chicago
Our customers tell us that they can't get enough of the sightseeing around Hilton Garden Inn Chicago Downtown/Magnificent Mile. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus an indoor pool and a restaurant.
Pool
Pet-friendly
citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is €191 per night
€191
22 Sept - 23 Sept
includes taxes & fees
0.37 km from Downtown Chicago
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
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is €161 per night
€161
22 Sept - 23 Sept
includes taxes & fees
1.65 km from Downtown Chicago
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
Freehand Chicago
19 East Ohio Street, Chicago, IL
The price is €139 per night
€139
23 Sept - 24 Sept
includes taxes & fees
0.74 km from Downtown Chicago
Our customers tell us that they can't get enough of the helpful staff at Freehand Chicago. 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.
Pet-friendly
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.
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Flights
^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.
