Uptown Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • payments icon
    Better together
    Save up to AU$703 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Your Uptown Holiday

Take the stress out of travel planning with an Uptown holiday package. With all the details organised before you set off, all you have to do is simply enjoy this residential neighbourhood's cafes, history and culture. Not sure what to see and do during your trip to Uptown? Nearby attractions like Lincoln Park, Loyola University Chicago and Aragon Ballroom are great places to start. Expedia can help you turn your ideal Uptown holiday into reality, no matter your travel plans or budget.

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

Our pick of the best Uptown Hotel Deals

Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is AU$172 per night from 20 Apr to 21 Apr
AU$172
includes taxes & fees
20 Apr - 21 Apr
8.6/10 Excellent! (1,000 reviews)
"did a last minute booking for a great price. everything you need was walking distance."

Reviewed on 31 Mar. 2025

Crowne Plaza Chicago West Loop by IHG
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$408 per night from 13 Apr to 14 Apr
AU$408
includes taxes & fees
13 Apr - 14 Apr
8.8/10 Excellent! (2,020 reviews)
"great location"

Reviewed on 31 Mar. 2025

Swissotel - Chicago
Embassy Suites by Hilton Chicago Downtown River North
Embassy Suites by Hilton Chicago Downtown River North
4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$252 per night from 20 Apr to 21 Apr
AU$252
includes taxes & fees
20 Apr - 21 Apr
8.2/10 Very Good! (3,816 reviews)
"nice room really liked it"

Reviewed on 1 Apr. 2025

Embassy Suites by Hilton Chicago Downtown River North
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

Activities

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