Uptown Vacations from ₩1,381,082

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The Latest Uptown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Pool fixed would be nicer.

Reviewed on Aug 10, 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
8.8/10 Excellent! (1,925 reviews)
Transport access walking distance to take train to midway airport was easy and convenient

Reviewed on Aug 7, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.2/10 Wonderful! (277 reviews)
Ran into some confusion with my credit card. It was used at check in and then they said they didn’t have it

Reviewed on Aug 9, 2025

The Royal Sonesta Chicago Downtown

The Royal Sonesta Chicago Downtown

4 out of 5
Downtown Chicago
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.2/10 Wonderful! (2,798 reviews)
Friendly Staff. Great location. What a view

Reviewed on Aug 9, 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Oct 23 - Oct 29
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.2/10 Wonderful! (1,831 reviews)
Our venue was close but once we were back to our hotel, it was our getaway!

Reviewed on Aug 8, 2025

Where to stay in Uptown

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

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
The price is ₩186,442 per night from Sep 1 to Sep 2
₩186,442
₩218,856 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,931 reviews)
"Restraint needs bigger menu"

Reviewed on Aug 9, 2025

Congress Plaza Hotel
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 ₩240,813 per night from Aug 21 to Aug 22
₩240,813
₩317,409 total
Aug 21 - Aug 22
includes taxes & fees
8.2/10 Very Good! (1,835 reviews)
"The property if beautiful and historic. The main room is incredible. The rooms are well taken care of, you can just tell they are a little dated with a slight smell. I would definitely stay here again."

Reviewed on Aug 8, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ₩213,107 per night from Aug 24 to Aug 25
₩213,107
₩250,165 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (3,640 reviews)
"Close to everything"

Reviewed on Aug 9, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,589 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 vacation package cost?
From as little as ₩1,381,082, 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. 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 to learn more.

Discover the most popular places to visit in Uptown

Autumn leaves frame historic building in Lincoln Park Chicago

Lincoln Park

This expansive public park along Lake Michigan offers museums, beaches, nature reserves and sporting facilities.

Lincoln Park
Navy Pier featuring a sunset and rides

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier
Millennium Park featuring a city, modern architecture and fall colors

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

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