Heart of Chicago Holidays

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Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
per person
12 Jun - 16 Jun
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8/10 Very Good! (1,524 reviews)
Front desk surprised me with a note & a bottle of wine for my birthday, as well as an early check in. Room was clean, bed was comfy. Only pit to this stay was that we were in an adjoining room so we felt like we had to be extra quiet. I should’ve looked into that before booking.

Reviewed on 8 Apr 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
per person
12 Jun - 16 Jun
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9/10 Wonderful! (295 reviews)
Safe, beautiful suite that includes full kitchen, staff was very kind

Reviewed on 8 Apr 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
12 Jun - 16 Jun
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,546 reviews)
Rooms were clean and spacious. Disappointed at the bar staff, not very engaging.

Reviewed on 6 Apr 2025

21c Museum Hotel Chicago

21c Museum Hotel Chicago

4 out of 5
Downtown Chicago
per person
12 Jun - 16 Jun
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (1,895 reviews)
Very nice Hotel. Very cozy! The staff is very attentive and respectful. Came in from out of town and I felt like I was home with the warm welcome. No complaints and a must to visit again. Hands down five star!

Reviewed on 10 Apr 2025

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
per person
12 Jun - 16 Jun
found 22 hours ago
Return direct flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (3,465 reviews)
Great place to stay in the Loop

Reviewed on 8 Apr 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 featuring a city

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Michigan Avenue and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

Find hotels in Downtown Chicago

Top hotels in Heart of 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 €137 per night from 21 Apr to 22 Apr
€137
includes taxes & fees
21 Apr - 22 Apr
8.2/10 Very Good! (3,856 reviews)
"Great place to stay for families. Breakfast is decent. A lot of dining options around the area. Pretty central to everything."

Reviewed on 9 Apr 2025

Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago
Swissotel - Chicago
4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is €194 per night from 16 Apr to 17 Apr
€194
includes taxes & fees
16 Apr - 17 Apr
8.8/10 Excellent! (2,033 reviews)
"Convenient location"

Reviewed on 7 Apr 2025

Swissotel - Chicago
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is €99 per night from 20 Apr to 21 Apr
€99
includes taxes & fees
20 Apr - 21 Apr
8.6/10 Excellent! (1,002 reviews)
Great place, no drawbacks
"Great hotel, great location, friendly staff. The bed was quite comfortable, and the small balcony was a nice little perk."

Reviewed on 8 Apr 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,251 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 €1,007. 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

River tour boat in Chicago

Architecture River Tour

€45
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

€41
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
Color Factory Chicago Ticket

Color Factory Chicago Ticket

€32
per adult
100% of travellers recommend
Color Factory Chicago Ticket
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.