
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
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Downtown Chicago
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour ago
Our customers tell us they can't get enough of Bluegreen Vacations Hotel Blake, Ascend Resort Collection's great location. During your stay, you're just a quick walk from State Street. 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
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour 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
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour 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
Omni Chicago Hotel
Downtown Chicago
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour ago
Our customers tell us that they can't get enough of the shopping around Omni Chicago Hotel. During your stay, you're just a quick walk from Michigan Avenue. Free WiFi in public areas, a restaurant and a 24-hour gym are available.

4.0-star property
Level Chicago - River North
Downtown Chicago
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour 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.
Uptown Holiday Packages for 4 Nights
Price found within the past 48 hours. Click for updated prices.

4.0-star property
Bluegreen Vacations Hotel Blake, Ascend Resort Collection
Downtown Chicago
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour ago
Our customers tell us they can't get enough of Bluegreen Vacations Hotel Blake, Ascend Resort Collection's great location. During your stay, you're just a quick walk from State Street. 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
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour 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
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour 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
Omni Chicago Hotel
Downtown Chicago
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour ago
Our customers tell us that they can't get enough of the shopping around Omni Chicago Hotel. During your stay, you're just a quick walk from Michigan Avenue. Free WiFi in public areas, a restaurant and a 24-hour gym are available.

4.0-star property
Level Chicago - River North
Downtown Chicago
1 Oct - 5 Oct
4 night stay
Zürich (ZRH) to Chicago (ORD)
Icelandair • Direct return • Coach
per person
found 1 hour 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.
Best Uptown hotel deals for your holiday

Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
The price is CHF 167 per night
CHF 167
4 Aug - 5 Aug
includes taxes & fees
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.

InterContinental Chicago Magnificent Mile by IHG
505 N Michigan Ave, Chicago, IL
The price is CHF 260 per night
CHF 260
24 Jul - 25 Jul
includes taxes & fees
8.66 km from Uptown
Our customers tell us they can't get enough of InterContinental Chicago Magnificent Mile by IHG's great location. During your stay, you're just a quick walk from Michigan Avenue. Enjoy features like free WiFi in public areas, plus 2 restaurants and an indoor pool.

Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
The price is CHF 136 per night
CHF 136
10 Aug - 11 Aug
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

Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
The price is CHF 181 per night
CHF 181
17 Aug - 18 Aug
includes taxes & fees
8.4 km from Uptown
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.

Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
The price is CHF 154 per night
CHF 154
10 Aug - 11 Aug
includes taxes & fees
9.45 km from Uptown
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.

citizenM Chicago Downtown
80 East Wacker Place, Chicago, IL
The price is CHF 159 per night
CHF 159
4 Aug - 5 Aug
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.
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.
Cheap flights to Uptown
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LAX
Los Angeles
ORD
Chicago
CHF 225 Return, found 5 days ago
CHF 225
Return
found 5 days ago
LAX
Los Angeles
ORD
Chicago
CHF 261 Return, found 2 days ago
CHF 261
Return
found 2 days ago
LAX
Los Angeles
ORD
Chicago
CHF 265 Return, found 5 days ago
CHF 265
Return
found 5 days ago
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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.