Heart of Chicago Holidays
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Our guide on where to stay in Heart of Chicago
Find the best Heart of Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Heart of 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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
An avenue brimming with superb shops and restaurants, the Magnificent Mile more than lives up to its name.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Our pick of the best Heart of Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
NZ$212
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,186 reviews)
"n/a"
Reviewed on 14 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
NZ$290
31 Aug - 1 Sept
includes taxes & fees
8/10 Very good! (1,985 reviews)
"I was unhappy about my stay in the hotel. Upon arrival I left my car for vallet service in the front of the hotel at 11 45 pm. And provided the keys to receptionist as I had urgent conference call. He told me that parking person busy with other car and will come shortly and take the keys from him. ..."
Reviewed on 14 Aug 2026
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
NZ$479
4 Sept - 5 Sept
includes taxes & fees
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 a Heart of Chicago holiday package cost?
From as little as . Yes, you read that right. Our Heart of Chicago packages are the easiest way to make your budget stretch further. Combine your preferred hotels, flights and car rentals and get out and explore this exciting destination.
How do I get a cheap travel package to Heart of Chicago?
One of the easiest ways to save dollars (and time) is to bundle your bookings with Expedia. Hotels, flights, activities and rental cars — we've got everything you need. Pick and choose a combination that suits you and watch your savings grow. Of course, a package deal is never one-size-fits-all. That's why we offer more than 550 air carriers and 1 000 000 hotels across the world, which lets you customize your Heart of Chicago holiday.
Where should I stay in Heart of Chicago?
Holiday Makers come from all over to see University of Illinois Chicago and United Centre in Heart of Chicago. Book a hotel near these fantastic attractions to make sightseeing easy.
How far in advance should I book my Heart of Chicago holiday?
Be rewarded with the biggest variety and the cheapest prices by booking your holiday to Heart of Chicago early. Airlines generally sell tickets anywhere up to 12 months before departure, so start locking things in as soon as you can. That being said, Expedia is constantly working to give you the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Heart of Chicago travel package include?
Car rentals, hotels and flights — we bring you the very best deals. All you'll have to do is pick and choose your ideal combination. Once you've made your booking, you can add on the exciting stuff like activities and sightseeing tours. Our travel packages make it easy to customize an exciting Heart of Chicago escape.
What should I know before booking a Heart of Chicago travel package?
A travel package can be more affordable than separately booking all you need for your trip. For example, combine your flights, hotels and rental cars and score big savings. Whatever your holiday plans, you'll find a package to suit your budget.
Can I choose my airline with a Heart of Chicago Expedia holiday package?
Yes, you're in charge. We offer more than 550 airlines worldwide, so you can design your Heart of Chicago getaway according to your travel preferences.
If I'm not able to travel, can I cancel my Heart of Chicago holiday package?
Yes, you can. We get that even the best-laid plans can fail, so we're happy to help if you have to make changes to your Heart of Chicago holiday package. It may be possible to change or cancel your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may impose a fee if your booking was made more than 24 hours ago. Take a look at our Customer Service Portal for further information. Also, check your itinerary for the nitty-gritty on change fees.
Stay near popular Heart of Chicago attractions
Canalport Riverwalk Park
After visiting Canalport Riverwalk Park, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.
National Museum of Mexican Art
You can spend time exploring the galleries in National Museum of Mexican Art during your travels in Chicago. Experience the acclaimed art galleries and entertainment choices in this vibrant area.
The Geraghty
After visiting The Geraghty, make a plan to see the other sights and activities in Chicago. Experience the area's art scene and festivals.
Cooper Dual Language Academy
You can spend time studying the exhibits at Cooper Dual Language Academy during your travels in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art galleries.
Mexican Fine Arts Center Museum
You can spend an afternoon browsing the exhibits at Mexican Fine Arts Center Museum during your travels in Chicago. Stroll along the lakeside or experience the entertainment choices in this vibrant area.
St Adalbert Church
St Adalbert Church is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the acclaimed theatre scene and entertainment choices in this vibrant area.
Activities
Chicago: Navy Pier Centennial Wheel Ticket
NZ$42
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.