Uptown Trips (flight + hotel)

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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

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotel + flight trips in Downtown Chicago

Top hotels in Uptown

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P8,096 per night from 15 May to 16 May
P8,096
per night
15 May - 16 May
7.6/10 Good! (2,540 reviews)
"Good price"

Reviewed on Apr 29, 2024

Warwick Allerton - Chicago
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 P8,183 per night from 13 May to 14 May
P8,183
per night
13 May - 14 May
7.6/10 Good! (6,636 reviews)
"I loved my stay at the Congress Plaza Hotel! Check in was easy, especially since I got to check in at 12 noon, instead of 3PM. My room was very spacious and my king size bed was made up nicely and it was very comfortable too! There were plenty of towels in the pretty bathroom. The flatscreen TV was ..."

Reviewed on May 1, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P9,284 per night from 12 May to 13 May
P9,284
per night
12 May - 13 May
8.6/10 Excellent! (2,834 reviews)
"Loved the free water. Hotel staff (Pedro) was very friendly & helpful! The room was the perfect size for one person."

Reviewed on Apr 30, 2024

River Hotel
See all 4,127 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.

Popular places to visit

Image for 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
Image for Lincoln Park

Lincoln Park

A large public park on the edge of Lake Michigan, with museums, beaches, nature reserves, sports fields, and space galore to while away a few hours.

Lincoln Park
Image for 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

Things to do

Image for BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago

P2,490
Per adult
98% of travellers recommend
BYOB Spray Paint 'n' Sip at Studio W.I.P. Chicago
Image for Chicago Graceland Cemetery Audio Tour

Chicago Graceland Cemetery Audio Tour

P558
Per adult
Chicago Graceland Cemetery Audio Tour
Image for Skyline Lake Tour

Skyline Lake Tour

P1,932
Per adult
92% of travellers recommend
Skyline Lake Tour
See all activities in Chicago

More trip options

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