Uptown Holidays from AU$2,013

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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.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was AU$2,327, price is now AU$2,013 per person
AU$2,013
per person
26 Feb - 1 Mar
found 18 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great hotel and expect

Reviewed on 22 Jan 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was AU$3,201, price is now AU$2,822 per person
AU$2,822
per person
26 Feb - 1 Mar
found 19 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
The staff was great. Everybody was friendly. The room was beautifully appointed, although maybe a little too heavy on electronics. I don't think every light switch needs to be a touch pad. And there were one or two things we couldn't figure out, such as the lighted mirror on the credenza: don't know where the controls for that were hiding. These are minor issues and do not take away from the splendid funishings in the room.

Reviewed on 11 Jan 2026

Waldorf Astoria Chicago

Waldorf Astoria Chicago

5 out of 5
Downtown Chicago
Price was AU$2,960, price is now AU$2,612 per person
AU$2,612
per person
26 Feb - 1 Mar
found 18 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,000 reviews)
First time there. Staff was helpful and they provided excellent memorable service

Reviewed on 20 Jan 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was AU$2,389, price is now AU$2,110 per person
AU$2,110
per person
26 Feb - 1 Mar
found 18 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
Everything about this hotel is special. Great staff- awesome restaurant/bar. Location is perfect. This hotel is my destination every time I come to the city. Which is quite often.

Reviewed on 20 Jan 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was AU$2,856, price is now AU$2,545 per person
AU$2,545
per person
26 Feb - 1 Mar
found 18 hours ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.8/10 Exceptional! (1,001 reviews)
Yes didn’t know you get free breakfast

Reviewed on 4 Jan 2026

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$235 per night from 14 Feb to 15 Feb
AU$235
14 Feb - 15 Feb
includes taxes & fees
8/10 Very Good! (9,790 reviews)
Really interesting place, great price for the location too. Staff was very friendly.

Reviewed on 19 Jan 2026

Congress Plaza Hotel
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$270 per night from 1 Feb to 2 Feb
AU$270
1 Feb - 2 Feb
includes taxes & fees
8.4/10 Very Good! (2,541 reviews)
Great staff, good location .

Reviewed on 14 Jan 2026

Hilton Chicago
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 AU$184 per night from 5 Feb to 6 Feb
AU$184
5 Feb - 6 Feb
includes taxes & fees
8.4/10 Very Good! (5,583 reviews)
Always a great stay, clean, great breakfast, great pool.

Reviewed on 22 Jan 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,794 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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All Inclusive Holidays
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beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does an Uptown holiday package cost?
From as little as AU$2,013, 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

Activities

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

AU$60
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$73
per adult
92% of travellers recommend
Chicago Crime and Mob Bus 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.