Heart of Chicago Holidays

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Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
Price was €1,276, price is now €844 per person
€844
per person
4 Oct - 10 Oct
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,621 reviews)
Check in was easy and it felt very safe. Room was clean and was good sized for a Chicago hotel.

Reviewed on 21 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €1,927, price is now €1,160 per person
€1,160
per person
2 Nov - 7 Nov
found 1 day ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.

Reviewed on 19 Aug 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
Price was €1,428, price is now €866 per person
€866
per person
4 Oct - 10 Oct
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (2,028 reviews)
Everyone there was friendly and gave us a lot of places to go eat for our one year anniversary

Reviewed on 21 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was €1,968, price is now €1,235 per person
€1,235
per person
2 Nov - 7 Nov
found 2 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was €1,712, price is now €1,116 per person
€1,116
per person
4 Oct - 10 Oct
found 5 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
One of the tvs didnt work, and neither did the room phone. Dislike the texting communication, and having to go thru 3rd party just to call front desk.

Reviewed on 17 Aug 2025

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 which includes 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

Top hotels in Heart of Chicago

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 €190 per night from 14 Sept to 15 Sept
€190
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (9,006 reviews)
"Great history . Staff was excellent"

Reviewed on 19 Aug 2025

Congress Plaza Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €152 per night from 1 Sept to 2 Sept
€152
1 Sept - 2 Sept
includes taxes & fees
8.2/10 Very Good! (1,205 reviews)
"The pool could have been a bit better"

Reviewed on 19 Aug 2025

The Wade
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 €154 per night from 4 Sept to 5 Sept
€154
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (4,729 reviews)
"The hotel was wonderfully nestled downtown and an easy walk to sites and restaurants."

Reviewed on 18 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,740 properties in Heart of Chicago
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 €844. 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.

Popular places to visit

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.

Canalport Riverwalk Park

Things to do

Artisan Italian Pasta Class in Chicago

Artisan Italian Pasta Class in Chicago (Includes 3-Course Meal)

€103
per adult
Artisan Italian Pasta Class in Chicago (Includes 3-Course Meal)
Exclusive Sushi-Making Class in Chicago

Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)

€103
per adult
Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)
River tour boat in Chicago

Architecture River Tour

€36
per adult
96% of travellers recommend
Architecture River 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.