Heart of Chicago Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
Plan, book, travel with confidence
Better together
Save up to CA $775 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
Top Holiday Package Deals in Heart of Chicago
Price found within the past 48 hours. Click for updated prices.
Arlo Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug. 23 - Aug. 28
found 6 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,114 reviews)
The hotel was great and guest services were awesome. Noted my late arrival due to delayed flight. The hotel is right on Michigan and the bus stops right in front. The rooms are comfortable and well designed.
However, I wouldn't recommend eating at ALK. What a rip. for $6, I got about 10 spears of grilled asparagus! I know food prices and labor have gone up but this is ridiculous.
Reviewed on Jun. 8, 2024
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
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Grant Park and Navy Pier are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Heart of Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $205 per night from Jun. 18 to Jun. 19
CA $205
CA $240 total
includes taxes & fees
Jun 18 - Jun 19
7.6/10 Good! (6,869 reviews)
"Very classy historic hotel. Comfortable beds, clean rooms."
Reviewed on Jun. 8, 2024
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $286 per night from Jul. 1 to Jul. 2
CA $286
CA $335 total
includes taxes & fees
Jul 1 - Jul 2
8/10 Very Good! (2,365 reviews)
"I loved everything about this property. It was easy to take public transportation with nearby buses and trains.It was close to everywhere i wanted to be and see. Food was good, everything was spotless and smelled really good in the lobby and the suite. I was very comfortable and will definitely stay ..."
Reviewed on Jun. 5, 2024
River Hotel
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $224 per night from Jul. 7 to Jul. 8
CA $224
CA $262 total
includes taxes & fees
Jul 7 - Jul 8
8.6/10 Excellent! (2,956 reviews)
"Excellent property"
Reviewed on Jun. 6, 2024
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.
Explore other types of vacation packages
Frequently asked questions
Discover the most popular places to visit in Heart of Chicago
Wrigley Field
4.5/5(158 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Six Flags Great America
4.5/5(5 reviews)
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
McCormick Place
4.5/5(141 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Things to do
Odyssey Lake Michigan Premier Dinner Cruise
CA $255
Per adult
76% of travellers recommend
Chicago: City Minibus Tour with Optional Architecture Cruise
CA $64
Per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.