Uptown Holidays from £883
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Your Uptown Holiday
Take the stress out of travel planning with an Uptown holiday package. With every last detail organised before you take off, all you have to do is enjoy this residential neighbourhood'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 holiday looks like, you can make it a reality with Expedia.
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
£1,041
per person
24 Oct - 28 Oct
found 18 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
The property waa clean and spacious
Staff were very nice and helpful. The location was perfect a short walk or drive to alot of places ans the best of all was that
A Garrett's popcorn shop waa right across the street!
Reviewed on 11 Aug 2026
Where to stay in Uptown
Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
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.
Theatre District
While you're in Theatre District, take in top sights like Michigan Avenue or State Street, and hop on the metro to see more of the city at Washington Station or Monroe Station (Blue Line).
Top hotels in Uptown
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£93
8 Sept - 9 Sept
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£126
30 Aug - 31 Aug
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
£197
4 Sept - 5 Sept
includes taxes & fees
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 travel package cost?
Perhaps less than you imagined — from only £883, in fact! By bundling hotels, flights and car rentals into your own custom-made travel package, your trip to Uptown is just clicks away.
If I'm not able to travel, can I cancel my Uptown travel package?
We understand — life doesn't always go according to plan. If you've booked an Uptown travel package and have to cancel or amend it, we're here to help. It's always worth taking a look at our Customer Service Portal first for information. But generally, if you've taken out your package within 24 hours, you may be able to cancel or amend your itinerary free of charge. If it's been more than 24 hours, your airline, hotel or car rental company may impose a fee.
How do I get a cheap travel package to Uptown?
Bundle, bundle, bundle. Flights, rental cars and hotels — combine whatever you need into an Uptown travel package to save a pile of cash. Score even more bargains when you include extras such as experiences or tours to your booking. But that's not the only good part. You have the freedom to tailor your holiday your way. We offer over 550 partner airlines and 1,000,000 properties in all corners of the globe, so that everyone has an opportunity to travel and live out those holiday dreams.
Does Expedia offer Book Now, Pay Later Uptown holidays?
We do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in instalments. Simply click on the payment plan that suits best during the checkout process and take the stress out of budgeting for your next trip. Make sure you bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your holiday buck. Consider these flexible payment options below:
- Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If making small repayments each month works for you, pick this option during the checkout process.
- Pay in instalments holidays: If you want to pay off your getaway in multiple transactions, holidays paid in instalments might be right for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan from Klarna.
Where should I stay in Uptown?
Make sightseeing a breeze by staying in a hotel right around the corner from Uptown's fantastic attractions. Millennium Park and Wrigley Field are two traveller favourites.
What are the top hotels in Uptown?
Hyatt Regency Chicago and The Godfrey Hotel Chicago are two of the most sought-after hotels in Uptown. Why not have a look at the rates and facilities at each and then decide?
How far in advance should I book my Uptown holiday?
Search Expedia to compare international airfares as soon as possible. You can generally purchase a ticket up to 12 months prior to departure. If it's too early for your preferred air carrier, or you've left things to the last minute, don't worry. The lowest prices to Uptown occasionally appear just weeks before the date of departure.
What does an Expedia Uptown travel package include?
With Expedia, you can select a combination of hotels, car rentals and flights to create your ideal Uptown package. Once you've made your booking, you can add on the fun things like day tours and activities. Remember — the more you bundle, the more you stand to save!
What should I know before booking an Uptown travel package?
Find deals that suit your budget with an Expedia package. Hotels, flights, rental cars — we've got them all. You'll save a packet just for bundling your bookings. Whether you're heading away on a winter adventure or drinking cocktails on a beach, your ideal getaway is just a few clicks away.
Can I choose my airline with an Uptown Expedia travel package?
Yes, so take your pick! We have access to over 550 airlines throughout the world, so you can design your Uptown escape according to your travel preferences.
Stay near popular Uptown attractions
Aragon Ballroom
9.2/10 (10 reviews)
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
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 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.
Hutchinson Street Historic District
You can learn about the history of Chicago with a visit to Hutchinson Street Historic District. Experience the acclaimed art galleries and entertainment choices in this vibrant area.
Riviera Theatre
8.0/10 (1 review)
You can enjoy a show at Riviera Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Pegasus Players
You can get tickets for a performance at Pegasus Players on your trip to Chicago. Experience the acclaimed art galleries and entertainment choices in this vibrant area.
Aragon Entertainment Center
6.0/10 (1 review)
You can get tickets for a performance at Aragon Entertainment Center during your stay in Chicago. Experience the entertainment choices and acclaimed art galleries in this vibrant area.
Black Ensemble Theater
You can get tickets for a performance at Black Ensemble Theater on your trip to Chicago. Experience the area's theatre scene and live music.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.