Uptown Holidays

  • Plan, book, travel with confidence

  • Better together

    Save up to €185 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
Red Roof Inn PLUS+ Chicago - Willowbrook

Red Roof Inn PLUS+ Chicago - Willowbrook

2.5 out of 5
Price was €339, price is now €282 per person
€282
per person
1 May - 4 May
found 1 day ago
Return flight included
Orlando (MCO) to Chicago (ORD)
6.4/10 (1,004 reviews)
Check in was quick and simple. The room was clean and that's all i needed for a few hours until i went to the airport. The extra lock on the,door was broken. There also was a coffee pot, but no coffee in the room

Reviewed on 8 Feb 2026

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
Price was €433, price is now €352 per person
€352
per person
1 May - 4 May
found 1 day ago
Return flight included
Orlando (MCO) to Chicago (ORD)
8.6/10 Excellent! (1,633 reviews)
Its good and specious room with full of facilities.

Reviewed on 14 Feb 2026

DoubleTree by Hilton Chicago - Alsip

DoubleTree by Hilton Chicago - Alsip

4 out of 5
Price was €469, price is now €386 per person
€386
per person
1 May - 4 May
found 1 day ago
Return flight included
Orlando (MCO) to Chicago (MDW)
8.2/10 Very Good! (1,007 reviews)
When showering the water was warm not hot at all

Reviewed on 17 Feb 2026

Holiday Inn Express Rolling Meadows - Schaumburg Area by IHG

Holiday Inn Express Rolling Meadows - Schaumburg Area by IHG

2.5 out of 5
Price was €402, price is now €336 per person
€336
per person
1 May - 4 May
found 1 day ago
Return flight included
Orlando (MCO) to Chicago (ORD)
8.2/10 Very Good! (687 reviews)
Was super clean rooms,sheets and everything else.The staff was very nice .

Reviewed on 25 Nov 2025

Courtyard by Marriott Chicago Midway Airport

Courtyard by Marriott Chicago Midway Airport

3 out of 5
Bedford Park
Price was €475, price is now €399 per person
€399
per person
1 May - 4 May
found 1 day ago
Return flight included
Orlando (MCO) to Chicago (ORD)
8.2/10 Very Good! (1,001 reviews)
It was better than we thought it would be! They had really nice rooms for reasonable price. Clean and neat. Staff was friendly and easy check In/check out process!

Reviewed on 15 Feb 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 which includes 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 €188 per night from 13 Mar to 14 Mar
€188
13 Mar - 14 Mar
includes taxes & fees
8/10 Very Good! (9,906 reviews)
The room and hotel is a bit run down as most places over a century old

Reviewed on 18 Feb 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 €122 per night from 4 Mar to 5 Mar
€122
4 Mar - 5 Mar
includes taxes & fees
9.2/10 Wonderful! (3,361 reviews)
Breakfast was nice

Reviewed on 17 Feb 2026

Hotel Riu Plaza Chicago
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is €162 per night from 27 Feb to 28 Feb
€162
27 Feb - 28 Feb
includes taxes & fees
8.4/10 Very Good! (2,617 reviews)
It was great

Reviewed on 12 Feb 2026

Hilton Chicago
See all 4,752 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.

Frequently asked questions

How much does an Uptown holiday package cost?
From as little as €282, 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.

Popular places to visit

Chicago_AragonBallroom_553248621563220754

Aragon Ballroom

Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theatre scene.

Aragon Ballroom
Montrose Beach featuring a city, a coastal town and a 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
Montrose Harbor featuring bird life and a bay or harbour

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.

Montrose Harbor

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€22
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€34
per adult
92% of travellers recommend
Art Institute of Chicago
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

€21
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.