Title:  Uptown Vacation Packages & Trips 2025 from CA $493 | Expedia.ca

  

[Uptown Travel Guide](https://expedia.ca/Chicago-Uptown.dx6132444)[Hotels in Uptown](https://expedia.ca/Uptown-Chicago-Hotels.0-n6132444-0.Travel-Guide-Filter-Hotels)[Flights to Chicago](https://expedia.ca/Cheap-Flights-To-Chicago.d178248.Travel-Guide-Flights)[Things to do in Chicago](https://expedia.ca/Things-To-Do-In-Chicago.d178248.Travel-Guide-Activities)[Uptown Car Rentals](https://expedia.ca/Car-Rentals-In-Uptown.d6132444.Car-Rental-Guide)

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

# Uptown Vacation Packages

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

-   ## 
    
    Plan, book, travel with confidence
    

### 

Better together

Save up to CA $1,096 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

Plan, book, and manage your trip all in one place

## Top Holiday Package Deals in Uptown

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

![Hilton Grand Vacations Club Chicago Magnificent Mile](https://images.trvl-media.com/lodging/38000000/37650000/37641700/37641670/843f6e73_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Hilton Grand Vacations Club Chicago Magnificent Mile

Downtown Chicago

CA $493

per person

Nov 24 - Nov 26

found 11 hours ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (291 reviews)

Food price was high but everything was fine

Reviewed on Oct 4, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-26/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=37641670&paandie=true&dealMarker=1qy9L2f9MnB3Zlaf3cNbvtGth4dimyl4wdI_Iwor39JDPbQnvR501hYhKbWok29v)

![Pendry Chicago](https://images.trvl-media.com/lodging/1000000/990000/982600/982552/8007d2c6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Pendry Chicago

Downtown Chicago

CA $706

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.4/10 Exceptional! (1,085 reviews)

The bed was extremly comfortable Staff was very attentive. Highly recommend

Reviewed on Oct 7, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=982552&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRsUAMrsQOSB--l79H1WxTEiY3dNw35QXXJfCQLyQQHd-)

![Park Hyatt Chicago](https://images.trvl-media.com/lodging/1000000/30000/20700/20695/c7c718ca_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Park Hyatt Chicago

Downtown Chicago

CA $1,300

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.6/10 Exceptional! (1,002 reviews)

Awesome room amazing tub even better service

Reviewed on Oct 2, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=20695&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRmuZ4gY80S-q5ZhAOUcqqeABSTpAxz_ZbtF0CiV5-Vj_)

![theWit Chicago, a Hilton Hotel](https://images.trvl-media.com/lodging/3000000/2470000/2463500/2463437/018283db_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### theWit Chicago, a Hilton Hotel

Downtown Chicago

CA $645

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9/10 Wonderful! (1,004 reviews)

Clean room, friendly staff, great location and within walking distance from all shops!

Reviewed on Oct 7, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=2463437&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRtxPLEbTJu58gGHVC0IyGrP7WHGGthP-zTIoOQI6YXla)

![The Emily Hotel](https://images.trvl-media.com/lodging/20000000/19390000/19381200/19381112/e58430ff_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Emily Hotel

Downtown Chicago

CA $803

per person

Dec 29 - Jan 2

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Chicago (ORD)

9.2/10 Wonderful! (1,222 reviews)

Perfect location and atmosphere

Reviewed on Oct 7, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-29/2026-01-02/?FromAirport=YTO&Destination=ORD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=19381112&paandie=true&dealMarker=QpLfFRqLVDnisD62S_OWRgnWbCLt8O8NmfmyQzxmEwK20syKMjLx0ULhklDPgNDC)

## Where to stay in Uptown

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

![Downtown Chicago showing a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/332000/332072-Downtown-Chicago.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 hotel + flight trips in Downtown Chicago](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Downtown%20Chicago&DestID=6350699&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Magnificent Mile - River North](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/24000/24577-Magnificent-Mile.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Magnificent Mile

Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.

[Find hotel + flight trips in Magnificent Mile](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Magnificent%20Mile&DestID=800025&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![The Loop - Downtown featuring a river or creek](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/192000/192013-The-Loop-Downtown.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### The Loop

4.5/5(725 area reviews)

Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.

[Find hotel + flight trips in The Loop](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=The%20Loop&DestID=800024&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543369-chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### River North

Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.

[Find hotel + flight trips in River North](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=River%20North&DestID=6350695&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Chicago which includes modern architecture and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/54000/54398-Chicago.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Lincoln Park

5/5(20 area reviews)

Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.

[Find hotel + flight trips in Lincoln Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Lincoln%20Park&DestID=6059328&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Uptown Hotel Deals

![Congress Plaza Hotel](https://images.trvl-media.com/lodging/1000000/10000/6500/6452/a9ee91b7_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $179

CA $210 total

Nov 2 - Nov 3

includes taxes & fees

7.8/10 Good! (9,342 reviews)

"We did not use laundry service, and the front desk staff did not mention any availbale services"

Reviewed on Oct 7, 2025

[](https://expedia.ca/Hotel-Search?startDate=02%2F11%2F2025&endDate=03%2F11%2F2025&selected=6452&PinnedHotelID=6452&HadPinnedHotel=true&regionId=6132444)

![Freehand Chicago](https://images.trvl-media.com/lodging/10000000/9420000/9418300/9418281/3b3ade3c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Freehand Chicago

19 East Ohio Street, Chicago, IL

Fully refundableReserve now, pay when you stay

CA $100

CA $143 total

Nov 10 - Nov 11

includes taxes & fees

7.8/10 Good! (2,426 reviews)

"Excellent location, clean and good room partners"

Reviewed on Oct 6, 2025

[](https://expedia.ca/Hotel-Search?startDate=10%2F11%2F2025&endDate=11%2F11%2F2025&selected=9418281&PinnedHotelID=9418281&HadPinnedHotel=true&regionId=6132444)

![Embassy Suites by Hilton Chicago Downtown River North](https://images.trvl-media.com/lodging/1000000/20000/11600/11580/w3840h2859x0y0-5fc518eb_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

CA $214

CA $251 total

Nov 9 - Nov 10

includes taxes & fees

8.4/10 Very Good! (5,072 reviews)

"The onsite parking is worth the money compared to other lots. Walk where you can. The Embassy is in the perfect location for a lot of attractions."

Reviewed on Oct 9, 2025

[](https://expedia.ca/Hotel-Search?startDate=09%2F11%2F2025&endDate=10%2F11%2F2025&selected=11580&PinnedHotelID=11580&HadPinnedHotel=true&regionId=6132444)

[See all 4,562 properties in Uptown](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F10%2F2025&endDate=12%2F10%2F2025&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 Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

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

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.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 Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

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

> From as little as CA $493, you can custom build your Uptown vacation package. Simply combine hotels, flights and rental cars and we'll reward you with discounts.

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

> Crafting your own Uptown vacation package with Expedia is a smart way to save. We have over 550 airlines and 1,000,000 hotel options across the globe. With such a broad range to select from, you'll have no trouble pulling together your perfect escape.

### Where should I stay in Uptown?

> Cross Lincoln Park off your bucket list and then stay right around the corner. Experience the exciting atmosphere around this leading attraction and head there whenever the mood strikes!

### What are the top hotels in Uptown?

> When it comes to welcoming places to stay in Uptown, you can't go past [The Guesthouse Hotel](https://www.expedia.ca/Chicago-Hotels-The-Guesthouse-Hotel.h16578746.Hotel-Information). Be sure to browse our offers and land a great price.

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

> While not all air carriers advertise ticket prices early, it's usually possible to look up international airfares on Expedia up to 12 months in advance. This is the time when you'll nab some fantastic bargains. If you're purchasing tickets last minute, you might still get lucky. Sometimes the lowest prices emerge a few weeks before departure.

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

> Expedia has everything you need to lock in Uptown trip, but what goes into your package is entirely up to you. Pick from any combination of flights, rental cars and hotels. After some activities to keep you busy? Once you've made your booking, you can add them too. No matter your budget or style, there's a deal to match your needs.

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

> We already have low prices. However, you'll enjoy even better deals if you book your flights, hotels and car rentals together. With an Expedia package, you'll get transparent pricing and lots of choice.

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

> You sure can. Expedia has access to more than 550 airline partners around the world, so go with the carrier that's a good fit for your budget needs.

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

> It's good to know that you can cancel your Uptown booking if your plans have changed. Whether you'll incur a fee or not depends on your airline, hotel or car rental company. It may be possible to cancel or change for free if you booked in the last 24 hours. Visit our [Customer Service Portal](https://www.expedia.ca/service/?langid=4105) to learn more.

### Discover the most popular places to visit in Uptown

![Montrose Beach which includes a city, a sandy beach and a coastal town](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/298000/298066-Montrose-Beach.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.ca/Montrose-Beach-Uptown.d6277595.Vacation-Attraction)

#### Aragon Ballroom

Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

[](https://expedia.ca/Aragon-Ballroom-Uptown.d553248621563220754.Vacation-Attraction)

#### Riviera Theatre

You can enjoy a show at Riviera Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.

[](https://expedia.ca/Riviera-Theatre-Uptown.d553248621555594761.Vacation-Attraction)

### Things to do

![River tour boat in Chicago](https://mediaim.expedia.com/localexpert/170432/2ab44ef1-1211-4f4f-9436-ce9a14d4241f.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Architecture River Tour

CA $67

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/architecture-river-tour.a170432.activity-details)

![Relax and enjoy the view](https://mediaim.expedia.com/localexpert/46106377/6686561e-a3aa-4cbf-9e71-f553bde2fa06.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Chicago Architecture Center River Cruise aboard First Lady

CA $77

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/chicago-architecture-center-river-cruise-aboard-first-lady.a46106377.activity-details)

![Color Factory Chicago Ticket](https://mediaim.expedia.com/localexpert/49191714/1b6e1be3-a6ba-4b3d-8e57-4d0336c3fd23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Color Factory Chicago Ticket

CA $47

per adult

**94%** of travellers recommend

[](https://expedia.ca/things-to-do/color-factory-chicago-ticket.a49191714.activity-details)

[See all activities in Chicago](https://expedia.ca/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.