
Cheap Holidays to Uptown
- Top deals for trips to Uptown
- 3-night holiday deals
- 4-night holiday deals
- 5-night holiday deals
- 6 or 7-night holiday deals
Top deals for trips to Uptown
Price found within the past 48 hours. Click for updated prices.

4.0-star property
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 883, price is now CHF 654 per person
CHF 654
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 24-hour gym, a bar and breakfast (surcharge). This property offers pet-friendly amenities, such as food and water bowls.

3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 999, price is now CHF 704 per person
CHF 704
per person
found 1 day 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
Pendry Chicago
Downtown Chicago
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 1'069, price is now CHF 798 per person
CHF 798
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
Swissotel - Chicago
Downtown Chicago
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 972, price is now CHF 727 per person
CHF 727
per person
found 1 day ago
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.

4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 890, price is now CHF 670 per person
CHF 670
per person
found 1 day ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North's great location. 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.
Uptown Holiday Packages for 5 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
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 883, price is now CHF 654 per person
CHF 654
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 24-hour gym, a bar and breakfast (surcharge). This property offers pet-friendly amenities, such as food and water bowls.

3.5-star property
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 999, price is now CHF 704 per person
CHF 704
per person
found 1 day 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
Pendry Chicago
Downtown Chicago
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 1'069, price is now CHF 798 per person
CHF 798
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
Swissotel - Chicago
Downtown Chicago
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 972, price is now CHF 727 per person
CHF 727
per person
found 1 day ago
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.

4.5-star property
The Royal Sonesta Chicago River North
Downtown Chicago
20 Dec - 25 Dec
5 night stay
Zürich (ZRH) to Chicago (ORD)
Austrian Airlines • Direct • Coach
Chicago (ORD) to Zürich (ZRH)
Lufthansa • Direct • Coach
Price was CHF 890, price is now CHF 670 per person
CHF 670
per person
found 1 day ago
Our customers tell us they can't get enough of The Royal Sonesta Chicago River North's great location. 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.
Best Uptown hotel deals for your holiday

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
10.37 km from Uptown
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.
Kostenloses WLAN
Restaurant

Freehand Chicago
19 East Ohio Street, Chicago, IL
The price is CHF 118 per night
CHF 118
21 Oct - 22 Oct
includes taxes & fees
8.44 km from Uptown
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.
Haustierfreundlich
Kostenloses WLAN

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is CHF 150 per night
CHF 150
20 Oct - 21 Oct
includes taxes & fees
7.8 km from Uptown
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.
Haustierfreundlich
Kostenloses WLAN

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is CHF 170 per night
CHF 170
28 Sept - 29 Sept
includes taxes & fees
9.09 km from Uptown
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.
Kostenloses WLAN
Restaurant

Hilton Garden Inn Chicago Downtown/Magnificent Mile
10 E Grand Ave, Chicago, IL
The price is CHF 168 per night
CHF 168
2 Oct - 3 Oct
includes taxes & fees
8.53 km from Uptown
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
Haustierfreundlich

The Allegro Royal Sonesta Hotel Chicago Loop
171 W Randolph St, Chicago, IL
The price is CHF 207 per night
CHF 207
2 Oct - 3 Oct
includes taxes & fees
9.21 km from Uptown
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.
Haustierfreundlich
Klimaanlage
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.
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^Savings based on all package bookings with Flight + Hotel made on ebookers.ch 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.