Uptown Holidays from AU$1,583

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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.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,541, price is now AU$1,583 per person
AU$1,583
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (455 reviews)
Great and helpful staff very clean, a place where you don’t feel out of place

Reviewed on 25 Apr 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,846, price is now AU$1,889 per person
AU$1,889
per person
28 May - 1 June
found 20 hours ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9/10 Wonderful! (463 reviews)
Great spot for small families that may need a space for than just sleeping

Reviewed on 27 Apr 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,926, price is now AU$1,953 per person
AU$1,953
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Kind staff and helpful, nice rooms, wish there was a fridge in the room.

Reviewed on 27 Apr 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$3,023, price is now AU$2,020 per person
AU$2,020
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (932 reviews)
Espectacular todo limpio seguro amables

Reviewed on 27 Apr 2026

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$3,055, price is now AU$2,186 per person
AU$2,186
per person
28 May - 1 June
found 1 day ago
Return flight included
Los Angeles (LAX) to Chicago (ORD)
9.2/10 Wonderful! (3,002 reviews)
Amazing location, great staff, room was luxurious, doormen were super friendly and helpful!

Reviewed on 24 Apr 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

Downtown Chicago

4 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

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$187 per night from 25 May to 26 May
AU$187
25 May - 26 May
includes taxes & fees
8.2/10 Very Good! (2,654 reviews)
It was ok

Reviewed on 28 Apr 2026

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is AU$210 per night from 25 May to 26 May
AU$210
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,143 reviews)
Everything was great until morning then our room filled up with smoke otherwise it was good

Reviewed on 27 Apr 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$163 per night from 25 May to 26 May
AU$163
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (3,471 reviews)
Quite. Clean, Safe

Reviewed on 27 Apr 2026

Club Quarters Hotel, Central Loop, Chicago
See all 4,742 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$1,583, 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

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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

AU$38
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

AU$61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

AU$56
per adult
92% 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.