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
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €825, price is now €662 per person
€662
per person
found 16 hours ago
The shopping around Sable at Navy Pier Chicago, Curio Collection by Hilton gets high marks from our customers. During your stay, you'll be connected to the convention centre and just a quick walk from Lake Michigan. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €970, price is now €697 per person
€697
per person
found 16 hours ago
Our customers tell us that they can't get enough of the helpful staff at Hilton Grand Vacations Club Chicago Magnificent Mile. 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.
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €946, price is now €682 per person
€682
per person
found 16 hours ago
Our customers tell us that they can't get enough of the helpful staff at theWit Chicago, a Hilton Hotel. During your stay, you're just a quick walk from Michigan Avenue. Features include 2 bars, a full-service spa and a restaurant.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €1,036, price is now €757 per person
€757
per person
found 16 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.
4.5-star property
Pendry Chicago
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €1,006, price is now €745 per person
€745
per person
found 16 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.
Downtown Chicago Holiday Packages for 5 Nights
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €825, price is now €662 per person
€662
per person
found 16 hours ago
The shopping around Sable at Navy Pier Chicago, Curio Collection by Hilton gets high marks from our customers. During your stay, you'll be connected to the convention centre and just a quick walk from Lake Michigan. You'll find features such as free WiFi in public areas, plus 2 restaurants and 2 bars.
3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €970, price is now €697 per person
€697
per person
found 16 hours ago
Our customers tell us that they can't get enough of the helpful staff at Hilton Grand Vacations Club Chicago Magnificent Mile. 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.
4.5-star property
theWit Chicago, a Hilton Hotel
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €946, price is now €682 per person
€682
per person
found 16 hours ago
Our customers tell us that they can't get enough of the helpful staff at theWit Chicago, a Hilton Hotel. During your stay, you're just a quick walk from Michigan Avenue. Features include 2 bars, a full-service spa and a restaurant.
4.0-star property
Level Chicago – Old Town
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €1,036, price is now €757 per person
€757
per person
found 16 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.
4.5-star property
Pendry Chicago
Downtown Chicago
1 Feb - 6 Feb
5 night stay
Dublin (DUB) to Chicago (ORD)
TAP Portugal • Direct return • Coach
Price was €1,006, price is now €745 per person
€745
per person
found 16 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.
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
Embassy Suites by Hilton Chicago Downtown River North
600 N State St Chicago IL
The price is €95 per night
€95
18 Dec - 19 Dec
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 Chicago/Magnificent Mile Suites
198 E Delaware Pl Chicago IL
The price is €107 per night
€107
15 Dec - 16 Dec
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
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
The price is €125 per night
€125
28 Dec - 29 Dec
includes taxes & fees
0.6 km from Downtown Chicago
Our customers tell us they can't get enough of Palmer House a Hilton Hotel's great location. During your stay, you're just a quick walk from Millennium Park. You'll find features such as a full-service spa, an indoor pool and a restaurant.
Pool
Spa
Club Quarters Hotel Wacker at Michigan, Chicago
75 E Wacker Dr Chicago IL
The price is €84 per night
€84
11 Dec - 12 Dec
includes taxes & fees
0.36 km from Downtown Chicago
Our customers tell us that they can't get enough of the helpful staff at Club Quarters Hotel Wacker at Michigan, Chicago. During your stay, you're just a quick walk from Chicago Riverwalk. You'll find features such as 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
Silversmith Hotel Chicago Downtown
10 S Wabash Ave Chicago IL
0.54 km from Downtown Chicago
Our customers tell us that they can't get enough of the comfortable beds at Silversmith Hotel Chicago Downtown. 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 24-hour gym and a bar.
Free WiFi
Air conditioning
The Royal Sonesta Chicago Downtown
71 E Wacker Dr Chicago IL
The price is €142 per night
€142
4 Jan - 5 Jan 2026
includes taxes & fees
0.34 km from Downtown Chicago
The sightseeing around The Royal Sonesta Chicago Downtown gets high marks from our customers. During your stay, you're just a quick walk from Chicago Riverwalk. You'll find features such as a restaurant, a 24-hour gym and a bar.
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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^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.