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A frozen river with a city skyline in the background.

Uptown Vacations

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ₩1,660,000 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Discover the most popular places to visit in Uptown

A historic theater with ornate architecture and a prominent marquee.

Aragon Ballroom

9.2/10 (10 reviews)
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its entertainment choices.

Uptown Hotel Deals

Rooftop terrace

The Guesthouse Hotel

The Guesthouse Hotel
4.0 star property
Uptown
9.8 out of 10, Exceptional, (407 reviews)
"I loved this hotel! It’s in a beautiful part of uptown Chicago (Andersonville- an adorable gayborhood), near lots of cute shops, thrift stores, pubs, and bakeries. It sits right across the street from a beautiful cemetery, filled with gorgeous old trees. The lobby is charming and welcoming, as is the rooftop deck, where you can see the Chicago skyline in the distance. The rooms are nicely decorated-tasteful, not overly adorned. Our room had a lovely balcony that we enjoyed. Beds were comfortable...
The price is ₩419,294
₩492,197 total
includes taxes & fees
Sep 2 - Sep 3
The Guesthouse Hotel
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.
See all properties in Uptown

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.