Uptown Holidays from £1,804

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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.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £2,531, price is now £1,804 per person
£1,804
per person
14 Jun - 21 Jun
found 2 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on 8 May 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,164, price is now £1,993 per person
£1,993
per person
31 Jul - 6 Aug
found 1 day ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
we didn't have breakfast at the hotel

Reviewed on 11 May 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £3,412, price is now £2,347 per person
£2,347
per person
31 Jul - 6 Aug
found 1 day ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
9.2/10 Wonderful! (973 reviews)
Great location nice rooms

Reviewed on 11 May 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was £2,599, price is now £1,894 per person
£1,894
per person
31 Jul - 6 Aug
found 1 day ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
London House Hilton Chicago was fabulous. Great location. Wonderful view nice rooms rooftop bar is amazing, make reservations. For a quieter atmosphere the lounge on the second floor is a great place to hang out.. We’ll definitely stay there again.

Reviewed on 11 May 2026

Urban Chicago Oasis

Urban Chicago Oasis

2 out of 5
Lakeview
Price was £2,515, price is now £1,877 per person
£1,877
per person
31 Jul - 6 Aug
found 1 day ago
Return direct flight included
Leeds (LBA) to Chicago (ORD)
No reviews

Where to stay in Uptown

Find the best Uptown areas and neighborhoods for the activities you enjoy most. Learn more about Uptown
Downtown Chicago

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
The price is £117 per night from 26 May to 27 May
£117
26 May - 27 May
includes taxes & fees
8/10 Very Good! (10,215 reviews)
We had a king bed facing the lake. The room was large but only one lamp near the bed and the other - very dim. Bathtub was inoperable, and no ventilation in the bathroom. Parking was easy, desk staff not very friendly.

Reviewed on 11 May 2026

Congress Plaza Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is £151 per night from 25 May to 26 May
£151
25 May - 26 May
includes taxes & fees
9.4/10 Exceptional! (4,115 reviews)
Great location & breakfast was amazing.

Reviewed on 11 May 2026

Hotel Riu Plaza Chicago
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 £131 per night from 25 May to 26 May
£131
25 May - 26 May
includes taxes & fees
9/10 Wonderful! (4,297 reviews)
The staff was very nice and attentive. The place was clean and quiet. Location is excellent. Very nice experience.

Reviewed on 11 May 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,685 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
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Beach Holidays
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Family Friendly Holidays

Frequently asked questions

How much does an Uptown travel package cost?
Perhaps less than you imagined — from only £1,804, 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

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£20
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

£32
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

£29
per adult
94% of travellers recommend
Art Institute of Chicago
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.