Uptown Holidays from AU$2,184

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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.
The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was AU$3,172, price is now AU$2,184 per person
AU$2,184
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.2/10 Wonderful! (2,052 reviews)
I had an amazing experience here! The staff—from valet to front desk to restaurant—was incredibly courteous, and Nate at the bar was a standout! My room was spotless, housekeeping was proactive, and guest services were top-tier. The area around the hotel is packed with restaurants, bars, and convenience stores—super walkable and fun. Only two minor cons: the terrace closes at 10 PM (wish it stayed open later), and the pool was closed during my visit. Still, this place blew me away. Highly recommend!

Reviewed on 31 Aug. 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$4,113, price is now AU$2,534 per person
AU$2,534
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.2/10 Wonderful! (1,192 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug. 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$5,610, price is now AU$3,478 per person
AU$3,478
per person
31 Oct - 7 Nov
found 1 day ago
Return direct flight included
Sydney (SYD) to Chicago (ORD)
9.4/10 Exceptional! (1,694 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on 29 Aug. 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$5,537, price is now AU$3,571 per person
AU$3,571
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!

Reviewed on 31 Aug. 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was AU$3,524, price is now AU$2,340 per person
AU$2,340
per person
20 Oct - 26 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on 27 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$354 per night from 15 Sept to 16 Sept
AU$354
15 Sept - 16 Sept
includes taxes & fees
Congress Plaza Hotel
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
The price is AU$302 per night from 3 Sept to 4 Sept
AU$302
3 Sept - 4 Sept
includes taxes & fees
Embassy Suites by Hilton Chicago Downtown River North
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$278 per night from 2 Sept to 3 Sept
AU$278
2 Sept - 3 Sept
includes taxes & fees
Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,723 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
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does an Uptown holiday package cost?
From as little as AU$2,184, 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$63
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$62
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.