Uptown Holidays from £819

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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

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was £1,124, price is now £819 per person
£819
per person
19 Mar - 24 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Room was clean, staff was so polite and kind and very helpful. We took our 3 year old daughter with us and they were kind to her and welcoming! (That means a lot - not all hotels are welcoming to small children.) they made sure to open the doors for us each time we came in with our stroller. We will absolutely be back to the Riu in Chicago! 10/10

Reviewed on 9 Feb 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,492, price is now £1,063 per person
£1,063
per person
12 Mar - 16 Mar
found 6 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Lovely room. Excellent staff.

Reviewed on 3 Feb 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was £1,566, price is now £1,180 per person
£1,180
per person
19 Mar - 24 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Gorgeous property, facilities, and location.

Reviewed on 6 Feb 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was £1,099, price is now £837 per person
£837
per person
19 Mar - 24 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!

Reviewed on 2 Feb 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,159, price is now £886 per person
£886
per person
19 Mar - 24 Mar
found 1 day ago
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Muriel at the front desk was extremely helpful and courteous, wonderful historic art deco building right on Michigan Ave., great location and views, really nice, spacious and clean room. Chateau Carbide on the 24th floor is definitely worth checking out, nice cozy areas to hang out, sit on a couch and have a drink while enjoying great views of the city. We also got a free ride from the hotel to the Shedd Aquarium.

Reviewed on 31 Jan 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 featuring 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 £77 per night from 11 Feb to 12 Feb
£77
11 Feb - 12 Feb
includes taxes & fees
8/10 Very Good! (9,848 reviews)
Wonderful hotel

Reviewed on 4 Feb 2026

Congress Plaza Hotel
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is £176 per night from 7 Mar to 8 Mar
£176
7 Mar - 8 Mar
includes taxes & fees
8.2/10 Very Good! (2,211 reviews)
Easy booking, they let me check in early which I needed it. Friendly staff, nice bed, good shower pressure, clean room. Just need some updating to make it brighter room. Overall satisfied with my stay.

Reviewed on 2 Feb 2026

Hilton Chicago O'Hare Airport
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is £88 per night from 22 Feb to 23 Feb
£88
22 Feb - 23 Feb
includes taxes & fees
8.4/10 Very Good! (5,643 reviews)
Positives- As my friend said as we went to breakfast “the people here are so nice and look happy to work here!” I agree! Eloisa (I hope that is correct-our bartender ) made happy hour on Friday night even happier! She was friendly and knowledgeable, suggesting drinks we hadn’t had before just by ...

Reviewed on 8 Feb 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,756 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does an Uptown travel package cost?
Perhaps less than you imagined — from only £819, 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.

Popular places to visit

Montrose Beach showing a beach, a coastal town and a city

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: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
Chicago C3® : Save on admission to your choice of 3 top attractactions

Chicago C3® by CityPASS®

£79
per adult
90% of travellers recommend
Chicago C3® by CityPASS®
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. Flight-inclusive packages are ATOL protected.