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

Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$331 per night from 15 Jan to 16 Jan
NZ$331
15 Jan - 16 Jan 2026
includes taxes & fees
8.4/10 Very Good! (2,417 reviews)
Check in staff were great and room was clean. Worst part was house cleaner knocking at door at 1030am, after being up till 2am night before have a good time at football game. Hot tub amazing and our view!

Reviewed on 27 Dec 2025

Hilton Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$181 per night from 6 Jan to 7 Jan
NZ$181
6 Jan - 7 Jan 2026
includes taxes & fees
8.8/10 Excellent! (3,616 reviews)
Clean room. Separate bedroom from living room. Booked stay as my son had early appt at children’s hospital. Very accessible location.

Reviewed on 30 Dec 2025

Hilton Chicago/Magnificent Mile Suites
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NZ$331 per night from 26 Jan to 27 Jan
NZ$331
26 Jan - 27 Jan 2026
includes taxes & fees
8.4/10 Very Good! (2,176 reviews)
Room is gorgeous!!

Reviewed on 27 Dec 2025

Palmer House a Hilton Hotel
See all 4,757 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

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 entertainment choices and acclaimed theatre scene 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 entertainment choices.

Aragon Ballroom

Activities

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

NZ$42
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

NZ$70
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

NZ$84
per adult
92% of travellers recommend
Chicago Crime and Mob Bus 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.