Title: Uptown Holidays 2026 from £861 | Expedia.co.uk

[Hotels in Uptown](https://expedia.co.uk/Uptown-Chicago-Hotels.0-n6132444-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.co.uk/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.co.uk/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Uptown Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Uptown.d6132444.Car-Hire-Guide)

![](https://images.trvl-media.com/place/6132444/bc1230a6-8e59-4c7a-b058-9b6381d46b9e.jpg?impolicy=fcrop&w=1200&h=300&q=medium)

# Uptown Holidays from £861

## Book a Hotel + Flight or Car together to unlock savings

- ##  
Plan, book, travel with confidence
- ###  
Better together  
Save up to £335 when you book a flight and hotel together\*
- ###  
Find the right fit  
With over 300,000 hotels worldwide, it's easy to create a perfect package
- ###  
Rest easy  
Packages with flights are ATOL protected

### Your Uptown Holiday

Take the stress out of travel planning with an Uptown holiday package. With every last detail organised before you take off, all you have to do is enjoy this residential neighbourhood's cafes, history and culture. Hoping to head out and see the sights during your trip to Uptown? Don't miss nearby attractions like [Wrigley Field](https://www.expedia.co.uk/Wrigley-Field-Lakeview.d6034754.Attraction), [Lincoln Park](https://www.expedia.co.uk/Lincoln-Park-Uptown.d507390.Attraction) and [Loyola University Chicago](https://www.expedia.co.uk/Loyola-University-Chicago-Rogers-Park.d6182907.Attraction). No matter what your dream Uptown holiday looks like, you can make it a reality with Expedia.

Price found within the past 48 hours. Click for updated prices.

![Hotel Felix River North/Magnificent Mile](https://images.trvl-media.com/lodging/3000000/2230000/2222400/2222364/d891f039_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Felix River North/Magnificent Mile

Downtown Chicago

£861

per person

2 May - 4 May

found 23 hours ago

Return flight included

London (LHR) to Chicago (ORD)

8.2/10 Very Good! (2,582 reviews)

Very pet friendly. Small room but fine for the 2 overnights in city. The Shower head in 1003 leaks & reduced the flow but otherwise decent. Spot Hero parking ($35 night) around the corner for easy in and out. Central location to most areas of interest @$125 value

Reviewed on 24 Mar 2026

![Hotel Riu Plaza Chicago](https://images.trvl-media.com/lodging/103000000/102630000/102622800/102622712/3e21593f_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Riu Plaza Chicago

Downtown Chicago

£919

per person

2 May - 4 May

found 23 hours ago

Return flight included

London (LHR) to Chicago (ORD)

9.4/10 Exceptional! (3,495 reviews)

We loved everything about this modern hotel, with one exception: the room doors “bang” when closing. These sounds can be heard up and down the hall and woke us up multiple times. Recommendation to the property management to install some form of sound mitigation or softer closing mechanism in the doors.

Reviewed on 27 Mar 2026

![Trump International Hotel & Tower Chicago](https://images.trvl-media.com/lodging/2000000/1730000/1723300/1723215/4465cc02_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Trump International Hotel & Tower Chicago

Downtown Chicago

£1,090

per person

2 May - 4 May

found 23 hours ago

Return flight included

London (LHR) to Chicago (ORD)

9.4/10 Exceptional! (1,852 reviews)

Elegant and beautiful

Reviewed on 26 Mar 2026

![LondonHouse Chicago, Curio Collection by Hilton](https://images.trvl-media.com/lodging/13000000/12790000/12786700/12786616/7aab5ae1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

£1,004

per person

2 May - 4 May

found 23 hours ago

Return flight included

London (LHR) to Chicago (ORD)

9.4/10 Exceptional! (3,646 reviews)

If you want to be central to downtown Chicago this is the hotel. I really enjoyed my stay. Great rooftop bar and 2 attached restaurants you can go to if you don't want to travel outside the hotel. However, the hotel pillows are trash. Bring your own pillow if you dont want a stiff neck

Reviewed on 25 Mar 2026

![Hotel Saint Clair- Magnificent Mile](https://images.trvl-media.com/lodging/1000000/50000/50000/49985/c230295e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hotel Saint Clair- Magnificent Mile

Downtown Chicago

£884

per person

2 May - 4 May

found 23 hours ago

Return flight included

London (LHR) to Chicago (ORD)

8.4/10 Very Good! (1,862 reviews)

Front desk people are out of this world, they are here for the customer.

Reviewed on 26 Mar 2026

## Where to stay in Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most. [Learn more about Uptown](https://expedia.co.uk/Chicago-Uptown.dx6132444)

![Downtown Chicago](https://images.trvl-media.com/place/6350699/f8ae2db6-94cc-4898-aa46-e275588c3787.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Downtown Chicago

5 out of top 10 points of interest in this area

 The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art. 

[Find hotels in Downtown Chicago](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=6350699)

![Magnificent Mile](https://images.trvl-media.com/place/800025/2f4bc1ac-f370-4b72-8a89-0aa7dcb93f0c.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Magnificent Mile

 Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes. 

[Find hotels in Magnificent Mile](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=800025)

![The Loop](https://images.trvl-media.com/place/800024/9e323a45-98da-4519-b5ca-71275e70174f.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### The Loop

4.5/5(189 area reviews)

 Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean. 

[Find hotels in The Loop](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=800024)

![Underground passage in the Chicago O'Hare airport](https://images.trvl-media.com/place/553248635074842747/1dda5453-2f05-4485-9f3c-404a7075d270.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### O'Hare

3.5/5(10 area reviews)

 Travellers choose O'Hare for its abundant dining options. Hop aboard the metro at Cumberland Station or Remote Parking Station and check out top sights like Fashion Outlets of Chicago. 

[Find hotels in O'Hare](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=553248635074842747)

![River North](https://images.trvl-media.com/place/6350695/b009c703-f7ab-4e4c-95a4-4b883071adef.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### River North

 Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city. 

[Find hotels in River North](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Dest.PKG.Neighborhoods&regionId=6350695)

## Top hotels in Uptown

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/11b63ec2_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Fully refundableReserve now, pay when you stay

£101

5 Apr - 6 Apr

includes taxes & fees

8/10 Very Good! (9,993 reviews)

I chose the hotel for the location to meet friends for a visit to the Art Institute and dinner as I passed through the city, a modest price and at-grade adjacent parking lot convenience, but the physical condition was so shabby. The mattress was too hard for me, so made for an uncomfortable sleep. ...

Reviewed on 27 Mar 2026

[](https://expedia.co.uk/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=6132444)

![Hilton Chicago/Magnificent Mile Suites](https://images.trvl-media.com/lodging/1000000/20000/18600/18514/a215cd17_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Fully refundableReserve now, pay when you stay

£121

9 Apr - 10 Apr

includes taxes & fees

9/10 Wonderful! (3,991 reviews)

We had booked the lake view king suite room which the view was not great. When we got into the room it was very hot and we tried to turn the ac on but the air blowing out was still hot. Definitely would not book there again

Reviewed on 27 Mar 2026

[](https://expedia.co.uk/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=18514&PinnedHotelID=18514&HadPinnedHotel=true&regionId=6132444)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/24d28405_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Fully refundableReserve now, pay when you stay

£129

5 Apr - 6 Apr

includes taxes & fees

8.6/10 Excellent! (5,777 reviews)

We ended up with the stomach bug while we were on vacation, but the staff was all so responsive and helpful to us - allowing a later check-out time and bringing us bleach wipes. The texting feature was very helpful!

Reviewed on 26 Mar 2026

[](https://expedia.co.uk/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=6132444)

[See all 4,663 properties in Uptown](https://expedia.co.uk/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%2F03%2F2026&regionId=6132444)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Holidays

[](https://expedia.co.uk/lp/theme-holidays/all-inclusive-holidays?rfrr=editorial.All_Inclusive%20Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Holidays

[](https://expedia.co.uk/lp/theme-holidays/beach-holidays?rfrr=editorial.Beach_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Friendly Holidays

[](https://expedia.co.uk/lp/theme-holidays/kid-friendly-holidays?rfrr=editorial.Family_Friendly%20Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Holidays

[](https://expedia.co.uk/lp/theme-holidays/golf-holidays?rfrr=editorial.Golf_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Holidays

[](https://expedia.co.uk/lp/theme-holidays/luxury-holidays?rfrr=editorial.Luxury_Holidays.click)

![gay friendly holidays](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

LGBTQ+ Holidays

[](https://expedia.co.uk/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ+_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Holidays

[](https://expedia.co.uk/lp/theme-holidays/romantic-holidays?rfrr=editorial.Romantic_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Holidays

[](https://expedia.co.uk/lp/theme-holidays/ski-holidays?rfrr=editorial.Ski_Holidays.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/22/hero-image-pet-friendly_copy.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Pet Friendly Holidays

[](https://expedia.co.uk/lp/theme-holidays/pet-friendly-holidays?rfrr=editorial.Pet_Friendly%20Holidays.click)

![Holiday in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Where to go when

[](https://expedia.co.uk/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click)

## Frequently asked questions

### How much does an Uptown travel package cost?

### If I'm not able to travel, can I cancel my Uptown travel package?

### How do I get a cheap travel package to Uptown?

### Does Expedia offer Book Now, Pay Later Uptown holidays?

> - Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If making small repayments each month works for you, pick this option during the checkout process.
> - Pay in instalments holidays: If you want to pay off your getaway in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
> - Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan from Klarna.

### Where should I stay in Uptown?

### What are the top hotels in Uptown?

### How far in advance should I book my Uptown holiday?

### What does an Expedia Uptown travel package include?

### What should I know before booking an Uptown travel package?

### Can I choose my airline with an Uptown Expedia travel package?

### Popular places to visit

![Montrose Beach](https://images.trvl-media.com/place/6277595/33eea866-186b-47ad-8add-7a479ffd7597.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Montrose Beach

Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities.

[](https://expedia.co.uk/Montrose-Beach-Uptown.d6277595.Attraction)

### Things to do

![360 CHICAGO Observation Deck ](https://mediaim.expedia.com/localexpert/170348/1cbf6a0b-f355-4f8a-a858-37fdc0668a64.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 360 CHICAGO Observation Deck

£19

per adult

**86%** of travellers recommend

[](https://expedia.co.uk/things-to-do/360-chicago-observation-deck.a170348.activity-details)

![Wendella's 90-min Chicago River Architecture Tour](https://mediaim.expedia.com/localexpert/766175/932beb0e-70fe-42a4-baff-df68960da73f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Wendella's 90-min Chicago River Architecture Tour

£30

per adult

**94%** of travellers recommend

[](https://expedia.co.uk/things-to-do/wendellas-90-min-chicago-river-architecture-tour.a766175.activity-details)

![Flyover in Chicago](https://mediaim.expedia.com/localexpert/50023979/095bdacd-a8be-4515-aac0-469239aa8c0a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Flyover in Chicago

£28

per adult

**98%** of travellers recommend

[](https://expedia.co.uk/things-to-do/flyover-in-chicago.a50023979.activity-details)

[See all activities in Chicago](https://expedia.co.uk/things-to-do/search?rid=6132444)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.