Heart of Chicago Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ฿27,000 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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

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 ฿4,466 per night from 29 Jun to 30 Jun
฿4,466
฿5,310 total
29 Jun - 30 Jun
includes taxes & fees
8/10 Very Good! (10,130 reviews)
"The facilities are very old, and there is a musty smell in the room."

Reviewed on 18 Jun 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is ฿4,226 per night from 28 Jun to 29 Jun
฿4,226
฿5,025 total
28 Jun - 29 Jun
includes taxes & fees
7.8/10 Good! (1,595 reviews)
"seems like we are visiting every other month to meet up with friends. We have already recommended this hotel many times and will definitely be staying again."

Reviewed on 19 Jun 2026

The Chicago Hotel Collection - Magnificent Mile
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is ฿5,213 per night from 28 Jun to 29 Jun
฿5,213
฿5,942 total
28 Jun - 29 Jun
includes taxes & fees
8.8/10 Excellent! (2,669 reviews)
"Hotel main trash service pickup was directly below my room window and was extremely loud when unloading and loading rolloff dumpsters at 4am. No way to sleep through the noise. Shuttle service was very good to and from the airport. Toilet clogged after one use with no plunger available. Remodeling ..."

Reviewed on 17 Jun 2026

Hyatt Regency O'Hare Chicago
See all 4,688 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 . 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.
See properties
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.