Uptown Holidays

Book a Hotel + Flight or Car together to unlock savings

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

5 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Uptown

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
7.8/10 Good! (9,384 reviews)
"This is a beautiful historic Chicago downtown hotel across the street from Grant Park. However, some of the rooms and hallways are in need of updating."

Reviewed on 1 Oct 2025

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Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is 2.563.747 ₫ per night from 4 Nov to 5 Nov
2.563.747 ₫
3.474.025 ₫ total
4 Nov - 5 Nov
includes taxes & fees
7.8/10 Good! (2,417 reviews)
Good for 3 nights
"The price was right, the location excellent for shopping, riverwalk, other attractions within walking distance. The rooms are tiny, the bar and breakfast inconsistent. The mattress was terrible and needs to be replaced. The lobby area is beautifully refurbished and a place to spend time reading, ..."

Reviewed on 30 Sept 2025

Freehand Chicago
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
The price is 4.596.018 ₫ per night from 4 Nov to 5 Nov
4.596.018 ₫
5.395.266 ₫ total
4 Nov - 5 Nov
includes taxes & fees
8.4/10 Very Good! (5,020 reviews)
"Hotel is great and they were very attentive to anything that was needed. I cant say enough about the staff. Chicago is one of this country's great walkable cities so the location provided great opportunity to easier get where you want to go."

Reviewed on 1 Oct 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,544 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 1null000null000 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

Montrose Beach showing a beach, a coastal town and a city

Montrose Beach

If a restful holiday is part of your travel plans, Montrose Beach might be the perfect place to visit during your trip to Chicago. Stroll along the lakeside or discover the area's sunrises.

Montrose Beach
Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

4.5/5(40 reviews)

Catch an event at Wrigley Field during your trip to Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.

Wrigley Field
McCormick Place

McCormick Place

4.5/5(36 reviews)

During your trip, find out what's happening in McCormick Place, a top convention centre in Chicago. Discover the acclaimed theatre scene and notable monuments in this vibrant area.

McCormick Place