Uptown Vacations

Book a Hotel + Flight or Car together to unlock savings

Your Uptown Vacation

Take the stress out of travel planning with an Uptown vacation package. With every last detail organized before you take off, all you have to do is enjoy this residential neighborhood's cafes, history and culture. Hoping to head out and see the sights during your trip to Uptown? Don't miss nearby attractions like Wrigley Field, Lincoln Park and Loyola University Chicago. No matter what your dream Uptown vacation looks like, you can make it a reality with Expedia.

The Latest Uptown Vacation Packages

Price found within the past 48 hours. Click for updated prices.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,002 reviews)
The hotel is beautiful and everything was so lovely.

Reviewed on May 27, 2024

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.2/10 Wonderful! (97 reviews)
Outstanding service and facility.

Reviewed on Jan 10, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,003 reviews)
Great location, great staff

Reviewed on May 27, 2024

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,003 reviews)
This hotel was very unique and attractive in a convenient location, really liked how easy everything was and straight forward

Reviewed on May 27, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 9 - Aug 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (207 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.

Reviewed on Mar 16, 2024

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

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotel + flight trips in Downtown Chicago

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 $167 per night from Jun 16 to Jun 17
$167
$196 total
includes taxes & fees
Jun 16 - Jun 17
7.6/10 Good! (6,802 reviews)
"No parking available"

Reviewed on May 24, 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 $169 per night from May 29 to May 30
$169
$198 total
includes taxes & fees
May 29 - May 30
8.6/10 Excellent! (2,911 reviews)
"Great place"

Reviewed on May 27, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $180 per night from May 29 to May 30
$180
$211 total
includes taxes & fees
May 29 - May 30
8.2/10 Very Good! (1,966 reviews)
"Great service and very convenient to get into city and shopping , dining and sign seeing"

Reviewed on May 27, 2024

Eurostars Magnificent Mile
See all 4,143 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Uptown vacation package cost?
From as little as $470, 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

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

4.5/5(554 reviews)

This expansive public park along Lake Michigan offers museums, beaches, nature reserves and sporting facilities.

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 Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$229
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
92% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

$89
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

Other vacations you might like

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