Uptown Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $1,096 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

Top Holiday Package Deals in Uptown

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Hotel Riu Plaza Chicago
Sable at Navy Pier Chicago, Curio Collection by Hilton
Sports Illustrated Resorts Chicago
Hotel Arista

Where to stay in Uptown

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

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 CA $159 per night from Apr 16 to Apr 17
CA $159
CA $186 total
Apr 16 - Apr 17
includes taxes & fees
8/10 Very Good! (9,991 reviews)
Building is not in good shape. Repairs that have been done have not been done well. Outlets and hinges painted over, fixtures that don't fit, and no hot water. Cheap furnishings and not clean. Do not recommend!

Reviewed on Mar 27, 2026

Congress Plaza Hotel
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 CA $169 per night from Apr 9 to Apr 10
CA $169
CA $199 total
Apr 9 - Apr 10
includes taxes & fees
9/10 Wonderful! (3,988 reviews)
I would def say please please clean around the pool where the water runs through on the side the stainless steel could use a nice scrub, doesn't look clean at all.

Reviewed on Mar 26, 2026

Hilton Chicago/Magnificent Mile Suites
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 CA $183 per night from Apr 12 to Apr 13
CA $183
CA $215 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (5,777 reviews)
We ended up with the stomach bug while we were on vacation, but the staff was all so responsive and helpful to us - allowing a later check-out time and bringing us bleach wipes. The texting feature was very helpful!

Reviewed on Mar 26, 2026

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 vacation package cost?
From as little as CA $1,013, 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

Things to do

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