Uptown Vacations from ₩2,291,740

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The Latest Uptown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I loved the location of the property, and the overall concept of something fun and funky, but I had a "higher end" room, and it was right near the elevator, so I got a lot of noise on that side, plus the El from the other side. The rug wasn't super clean (although the bedding and the rest of the room were a delight). The most annoying thing was the TV. Anything I turned it to, 10 minutes later to the minute, it went back to the Virgin channel #1, here are all our hotels in the world. I really hated having to stay on top of a show, when usually I want the tv on as background while I'm getting ready, etc. Also, this hotel's amenities were oversold, i.e., good luck getting on the rooftop, especially if you just wanted a quiet sip of a drink. I loved the cafe and the staff, though, everyone was very pleasant.

Reviewed on Jul 15, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Amazing customer service

Reviewed on Jul 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
This hotel is designed well and has a great little bar downstairs along with a nice restaurant/cafe adjacent to the property. The front desk girls are mostly helpful specifically Muriel who made my stay extremely comfortable and gave me tons of recs on eats, etc. I was so thankful to have her around! I had AC issues with a crazy rattling noise in my first room and was upgraded to another nicer room my last night there. Neither of the beds were very comfortable - I think adding a pillow top would be helpful! The rooms are cute though!

Reviewed on Jul 14, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Seoul (ICN) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Nice room and view. Rooftop was gorgeous

Reviewed on Jul 13, 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 ₩204,436 per night from Aug 5 to Aug 6
₩204,436
₩239,988 total
Aug 5 - Aug 6
includes taxes & fees
7.8/10 Good! (8,971 reviews)
Great Vacation!
"Loved Chicago and it was close to all the things we wanted to do. Able to walk everywhere and enjoy the water, parks, downtown area, etc."

Reviewed on Jul 14, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ₩275,486 per night from Aug 10 to Aug 11
₩275,486
₩367,648 total
Aug 10 - Aug 11
includes taxes & fees
9/10 Wonderful! (2,035 reviews)
Gorgeous and friendly
"Gorgeous hotel! Friendly staff, especially the door men were so helpful and fun. Had a small leak dripping water by the entrance of our room but they got it fixed in a timely manner."

Reviewed on Jul 13, 2025

InterContinental Chicago Magnificent Mile by IHG
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 ₩204,540 per night from Aug 10 to Aug 11
₩204,540
₩240,108 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (2,444 reviews)
"clean...close to attractions.."

Reviewed on Jul 14, 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,505 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 ₩2,291,740, 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

4.5/5(554 reviews)

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

4.5/5(4,870 reviews)

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

4.5/5(7,198 reviews)

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.