Uptown Holidays
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Where to stay in Uptown
Downtown Chicago
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Discover the most popular places to visit in Uptown
What to do near Uptown
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower
Uptown Hotel Deals
"The location is perfect for wandering around Andersonville's many small businesses (great restaurants and really cool shops) and is very close to a couple of playgrounds for the kids. There was the perfect amount of space for our two families in the "room" we chose and the staff were very accommodating and helpful with parking and extra stuff we forgot to bring - the only thing we wanted more of were coffee beans (we only had one serving on hand for our two night stay) and tea (we ran out of...
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites"The hotel was basically clean, with no funky smells, and the location was fabulous. The layout of the room was also great, giving us some privacy, and we loved the view of Lake Michigan. However, the room was tired and definitely needed an update. The plugs and USB ports on one side of the bed didn't work, as did one of the house phones. Also, the door stopper in the bathroom was completely rusted, and dirty looking. The bed, in terms of comfort was also meh. Decent, but the sheets...
Hampton Inn & Suites Chicago Downtown
Hampton Inn & Suites Chicago Downtown"Breakfaste are very well!"
Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent Mile
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG"All was great !!"
DoubleTree by Hilton Chicago - Magnificent Mile
DoubleTree by Hilton Chicago - Magnificent Mile"Everything about the stay was amazing from beginning to end . The restaurant inside was also pretty tasty and the staff was exceptional."
Hyatt Place Chicago/River North
Hyatt Place Chicago/River North
Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag MileFrequently 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.