Uptown Holidays from £962

Book a Hotel + Flight or Car together to unlock savings

    deals illustration
    Better together
    Save up to £335 when you book a flight and hotel together*
    stays illustration
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    luggage illustration
    Rest easy
    Plan, book, and manage your trip all in one place

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.
Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
9 Sept - 13 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,769 reviews)
Excellent location. Will stay there again.

Reviewed on 27 Jun 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
9 Sept - 13 Sept
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (1,623 reviews)
Pablo, the manager, got our great Chicago stay even better!

Reviewed on 24 Jun 2025

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
per person
12 Sept - 19 Sept
found 1 day ago
Return direct flight included
Manchester (MAN) to Chicago (ORD)
9.2/10 Wonderful! (211 reviews)
other than the mold on the soap dispenser this hotel is beautiful

Reviewed on 27 Jun 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
12 Aug - 17 Aug
found 1 hour ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,065 reviews)
I could feel the bed shake every time the next to

Reviewed on 27 Jun 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
per person
9 Sept - 16 Sept
found 22 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (251 reviews)
The hotel is nice and located in a great area. It’s within walking distance to several points of interest. The staff were friendly and helpful. I really enjoyed my stay.

Reviewed on 13 May 2025

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

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 £141 per night from 1 Jul to 2 Jul
£141
1 Jul - 2 Jul
includes taxes & fees
8.4/10 Very Good! (4,279 reviews)
"Perfect property, everything is walkable distance"

Reviewed on 26 Jun 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is £157 per night from 1 Jul to 2 Jul
£157
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (1,921 reviews)
"We especially loved the room service, but the best was the unique indoor pool!!"

Reviewed on 25 Jun 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £123 per night from 7 Jul to 8 Jul
£123
7 Jul - 8 Jul
includes taxes & fees
8.8/10 Excellent! (2,343 reviews)
"It was good, clean and large room"

Reviewed on 27 Jun 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,454 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 £962, 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 Graceland Cemetery Audio Tour

Chicago Graceland Cemetery Audio Tour

£8
per traveller
Chicago Graceland Cemetery Audio Tour
River tour boat in Chicago

Architecture River Tour

£36
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£33
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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.