Uptown Trip

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Where to stay in Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
Downtown Chicago featuring a city

Downtown Chicago

4 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

Top hotels in Uptown

River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₹11,762 per night from 28 May to 29 May
₹11,762
per night
28 May - 29 May
8.6/10 Excellent! (2,887 reviews)
"Appreciated the easy of self serve check in and checkout. Did not have to stand in line. Only complaint is that the wait time for elevators is too long. Number iof elevators do not support number of guests"

Reviewed on 22 May 2024

River Hotel
Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₹12,350 per night from 28 May to 29 May
₹12,350
per night
28 May - 29 May
7.6/10 Good! (6,797 reviews)
"Great historical hotel which is undergoing massive updates at the time we visited. Whole wings were being done. Our room smelled of fresh paint. Large gaps under doors made privacy and noise an issue between guests. However, the panoramic view of the lakefront from the 10th was breathtaking and location ..."

Reviewed on 24 May 2024

Congress Plaza Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₹14,957 per night from 28 May to 29 May
₹14,957
per night
28 May - 29 May
8.2/10 Very Good! (1,953 reviews)
Outstanding Front desk staff and Hotel
"Very Nice Hotel, In the heart of Chicago. Friendly and professional staff and the vallet guys are top notch not to mention cool. You are legit in walking distance of some if not all of what Chicago has to offer in terms of touristy type tings."

Reviewed on 26 May 2024

Eurostars Magnificent Mile
See all 4,166 properties in Uptown
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.

Frequently asked questions

How much does an Uptown holiday package cost?
From as little as , you can custom build your Uptown holiday 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 holiday 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. Be sure to browse our offers and land a great price.
How far in advance should I book my Uptown holiday?
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 holiday 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 holiday 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 to learn more.

Popular places to visit

Image for Montrose Beach

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.

Montrose Beach
Image for Lincoln Park

Lincoln Park

4.5/5(13 reviews)

A large public park on the edge of Lake Michigan, with museums, beaches, nature reserves, sports fields, and space galore to while away a few hours.

Lincoln Park
Image for Montrose Harbor

Montrose Harbor

With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.

Montrose Harbor

More trip options

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.