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 which includes a city

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

Top hotels in Uptown

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 P10,674 per night from Sep 14 to Sep 15
P10,674
P12,531 total
Sep 14 - Sep 15
includes taxes & fees
7.8/10 Good! (8,973 reviews)
"The staff was fantastic—friendly, helpful, and attentive, which really made the stay more pleasant. The hotel itself, however, is clearly very old, and many features show their age. My room was small but nicely kept, and the lakeside view was absolutely stunning. The room door was very difficult ..."

Reviewed on Aug 13, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P9,840 per night from Sep 2 to Sep 3
P9,840
P12,970 total
Sep 2 - Sep 3
includes taxes & fees
8.4/10 Very Good! (1,851 reviews)
"Helpful staff, beautiful hotel in a great location!"

Reviewed on Aug 12, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is P8,152 per night from Sep 3 to Sep 4
P8,152
P9,569 total
Sep 3 - Sep 4
includes taxes & fees
8.4/10 Very Good! (3,675 reviews)
"Very classy safe snd clean"

Reviewed on Aug 12, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,614 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

Montrose Beach featuring a beach, a coastal town and general coastal views

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

Things to do

Chicago Graceland Cemetery Audio Tour

Chicago Graceland Cemetery Audio Tour

P624
per traveler
Chicago Graceland Cemetery Audio Tour
River tour boat in Chicago

Architecture River Tour

P2,411
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

P2,617
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.