Uptown Holidays

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Our guide on 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

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

Our pick of the best Uptown Hotel Deals

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! (9,307 reviews)
"Parking situation is ridicules, hallways carpet very filthy. I understand it’s an older hotel but needs to be kept up. Bathroom door didn’t even close."

Reviewed on 25 Sept 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 NZ$249 per night from 20 Oct to 21 Oct
NZ$249
20 Oct - 21 Oct
includes taxes & fees
7.8/10 Good! (2,388 reviews)
"It felt cozy and comfortable. The room was a little bit dusty and the night light was not working."

Reviewed on 24 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
Fully refundableReserve now, pay when you stay
The price is NZ$379 per night from 5 Oct to 6 Oct
NZ$379
5 Oct - 6 Oct
includes taxes & fees
8.4/10 Very Good! (4,985 reviews)
"Clean room, staff was friendly & helpful. Location was perfect for us"

Reviewed on 25 Sept 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,527 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.

Discover the most popular places to visit in Uptown

Lincoln Park showing heritage architecture, a park and a house

Lincoln Park

Chicago's biggest park has beaches to bathe, museums to muse, golf courses, walking trails and limitless ways to relax.

Lincoln Park
Hutchinson Street Historic District

Hutchinson Street Historic District

You can learn about the history of Chicago with a visit to Hutchinson Street Historic District. Experience the acclaimed art galleries and entertainment choices in this vibrant area.

Hutchinson Street Historic District

Aragon Ballroom

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

Aragon Ballroom

Activities

Learn from a pro and discover the world of spray paint!

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

NZ$77
per adult
100% of travellers recommend
BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago
Chicago Graceland Cemetery Audio Tour

Chicago Graceland Cemetery Audio Tour

NZ$19
per traveller
Chicago Graceland Cemetery Audio Tour
River tour boat in Chicago

Architecture River Tour

NZ$83
per adult
96% of travellers recommend
Architecture River Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.