Uptown Vacations

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  • Better together

    Save up to NT$25,000 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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    Plan, book, and manage your trip all in one place

Where to stay in Uptown

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

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 NT$4,300 per night from Jun 30 to Jul 1
NT$4,300
NT$5,112 total
Jun 30 - Jul 1
includes taxes & fees
8/10 Very Good! (10,251 reviews)
"The only negative I had with the hotel was that their food choices were limited, and there were not a lot of healthy options. I would have really appreciated more veg choices with the meals, and more salad options."

Reviewed on 2026/6/12

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is NT$4,573 per night from Jun 30 to Jul 1
NT$4,573
NT$5,437 total
Jun 30 - Jul 1
includes taxes & fees
7.8/10 Good! (1,568 reviews)
"I"

Reviewed on 2026/6/12

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is NT$5,028 per night from Jun 28 to Jun 29
NT$5,028
NT$5,731 total
Jun 28 - Jun 29
includes taxes & fees
8.8/10 Excellent! (2,656 reviews)
"I really liked it and recommend it."

Reviewed on 2026/6/12

Hyatt Regency O'Hare Chicago
See all 4,600 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 , 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

Montrose Beach

Montrose Beach

Soak up the sun with views of Lincoln Park and Lake Michigan at this city beach known for its fun sports and extensive amenities.

Montrose Beach
Montrose Harbor

Montrose Harbor

With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.

Montrose Harbor
Hutchinson Street Historic District

Hutchinson Street Historic District

You can learn about the history of Chicago when you stop by Hutchinson Street Historic District. Experience the acclaimed theater scene and entertainment choices in this vibrant area.

Hutchinson Street Historic District
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.