Uptown Holidays from AU$2,249

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Your Uptown Holiday

Take the stress out of travel planning with an Uptown holiday package. With all the details organised before you set off, all you have to do is simply enjoy this residential neighbourhood's cafes, history and culture. Not sure what to see and do during your trip to Uptown? Nearby attractions like Lincoln Park, Loyola University Chicago and Aragon Ballroom are great places to start. Expedia can help you turn your ideal Uptown holiday into reality, no matter your travel plans or budget.

Top Holiday Package Deals in Uptown

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 15 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (2,250 reviews)
it was good as usual

Reviewed on 8 Aug. 2025

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 15 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.2/10 Very Good! (2,084 reviews)
The room was comfortable and very quiet despite the proximity to the airport. I would have preferred a queen size bed, but the only available option was a double.

Reviewed on 9 Aug. 2025

Sonesta Chicago O'Hare Airport Rosemont

Sonesta Chicago O'Hare Airport Rosemont

3 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 15 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.6/10 Excellent! (1,537 reviews)
Sonesta was lovely. Easy check in. Nice room. Pillows not so great. Shuttle service was excellent as was all the staff!

Reviewed on 8 Aug. 2025

DoubleTree by Hilton Chicago Schaumburg

DoubleTree by Hilton Chicago Schaumburg

4 out of 5
per person
16 Oct - 23 Oct
found 15 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
7.4/10 Good! (1,009 reviews)
Very very quiet slept so good Needed pool and gym and cooking for myself

Reviewed on 7 Aug. 2025

Staybridge Suites Chicago O'Hare - Rosemont by IHG

Staybridge Suites Chicago O'Hare - Rosemont by IHG

3 out of 5
O'Hare
per person
16 Oct - 23 Oct
found 15 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
8.8/10 Excellent! (1,001 reviews)
Clean and quiet. Great location and close to ORD

Reviewed on 6 Aug. 2025

Our guide on 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

Our pick of the best Uptown Hotel Deals

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 AU$242 per night from 1 Sept to 2 Sept
AU$242
1 Sept - 2 Sept
includes taxes & fees
7.8/10 Good! (8,921 reviews)
"Took water awhile to get hot for shower, and parking is ridiculously expensive. Other than that enjoyed staying at hotel"

Reviewed on 8 Aug. 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$350 per night from 22 Aug to 23 Aug
AU$350
22 Aug - 23 Aug
includes taxes & fees
8.2/10 Very Good! (1,835 reviews)
"The property if beautiful and historic. The main room is incredible. The rooms are well taken care of, you can just tell they are a little dated with a slight smell. I would definitely stay here again."

Reviewed on 8 Aug. 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$276 per night from 24 Aug to 25 Aug
AU$276
24 Aug - 25 Aug
includes taxes & fees
8.4/10 Very Good! (3,635 reviews)
"I liked the security and safeness. I did not like that there was no valet/door person to help with bags, when spending thousands of dollars I would expect a door person to be there to assist with bags out of car and up to room and would also appreciate complimentary water each day not 2 bottles in ..."

Reviewed on 8 Aug. 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,724 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
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beach holidays
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Frequently asked questions

How much does an Uptown holiday package cost?
From as little as AU$2,249, 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.

Discover the most popular places to visit in Uptown

Montrose Beach featuring a coastal town, general coastal views 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
Lincoln Park showing heritage architecture, a park and a house

Lincoln Park

A large public park on the edge of Lake Michigan, with museums, beaches, nature reserves, sports fields, and space galore to while away a few hours.

Lincoln Park

Activities

Chicago Graceland Cemetery Audio Tour

Chicago Graceland Cemetery Audio Tour

AU$17
per traveller
Chicago Graceland Cemetery Audio Tour
River tour boat in Chicago

Architecture River Tour

AU$64
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

AU$69
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
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.