Heart of Chicago Holidays

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to €185 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place
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
per person
11 Aug - 17 Aug
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,763 reviews)
Lovely staff, nice room, and smells amazing.

Reviewed on 9 Jun 2025

Chicago River Side Suites

Chicago River Side Suites

2 out of 5
Downtown Chicago
Save 100% on your flight
per person
11 Aug - 17 Aug
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
10/10 Exceptional! (1 review)
Perfect location. The roads are very clean and most importantly the mattress was very comfortable. We had the option to use a non pet friendly rooms since I have allergies and got a room higher floor for a free upgrade. So far one of the best hotels I’ve ever stayed at.

Reviewed on 24 May 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
11 Aug - 17 Aug
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.4/10 Exceptional! (1,602 reviews)
Very pleased. Will stay again

Reviewed on 8 Jun 2025

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
per person
11 Aug - 17 Aug
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
8.8/10 Excellent! (1,750 reviews)
Small room was uncomfortable

Reviewed on 8 Jun 2025

Arlo Chicago

Arlo Chicago

4 out of 5
Downtown Chicago
per person
11 Aug - 17 Aug
just found
Return flight included
Dublin (DUB) to Chicago (ORD)
9.2/10 Wonderful! (1,757 reviews)
Great location! Comfy bed- pillows are amazing!

Reviewed on 10 Jun 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

5 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 €183 per night from 30 Jun to 1 Jul
€183
30 Jun - 1 Jul
includes taxes & fees
8.4/10 Very Good! (4,177 reviews)
"Free breakfast. Clean rooms, great stay! No complaints."

Reviewed on 7 Jun 2025

Embassy Suites by Hilton Chicago Downtown River North
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG
4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is €215 per night from 1 Jul to 2 Jul
€215
1 Jul - 2 Jul
includes taxes & fees
9/10 Wonderful! (1,861 reviews)
"Great location and excellent staff. Enjoyed our stayed."

Reviewed on 8 Jun 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites
3.5 out of 5
198 E Delaware Pl, Chicago, IL
The price is €142 per night from 8 Jul to 9 Jul
€142
8 Jul - 9 Jul
includes taxes & fees
8.8/10 Excellent! (2,288 reviews)
"Pool not working"

Reviewed on 9 Jun 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,560 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 €899. 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

Exclusive Sushi-Making Class in Chicago

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

€105
per adult
Exclusive Sushi-Making Class in Chicago (Includes 3-Course Meal)
River tour boat in Chicago

Architecture River Tour

€43
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€40
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.