Bloomingdale Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Your Bloomingdale Vacation

Book a custom vacation package to Bloomingdale and prepare to experience this exciting city how you like. Think about spending some time in the neighborhood of Medinah, which is good for golfing and a whole lot more. You'll want to sightsee during your trip to Bloomingdale. Carve out some time for leading attractions such as LEGOLAND® Discovery Center, The Water Works Indoor Water Park and TopGolf Chicago. Your ideal Bloomingdale vacation is just clicks away. Explore hotels, airfares and more on Expedia for a getaway that's tailored just for you.

Top Bloomingdale Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,667, price is now CA $1,255 per person
CA $1,255
per person
Apr 28 - May 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,140 reviews)
Truly one of our favorite stays! The staff makes you feel at home & are super accommodating. I will stay here every time! The bellman Michael is quite literally the best ever!! He made our stay so wonderful and special!

Reviewed on Mar 16, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $2,263, price is now CA $1,452 per person
CA $1,452
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
It was in a perfect spot for us to visit Chicago and have a comfortable place to stay

Reviewed on Mar 21, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,331, price is now CA $1,504 per person
CA $1,504
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Great location, views, & amenities.

Reviewed on Mar 20, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,717, price is now CA $1,289 per person
CA $1,289
per person
Jun 5 - Jun 8
found 18 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (441 reviews)
Spacious room with great views and washer and dryer

Reviewed on Mar 17, 2026

Hilton Garden Inn Chicago Central Loop

Hilton Garden Inn Chicago Central Loop

3 out of 5
Downtown Chicago
Price was CA $1,928, price is now CA $1,458 per person
CA $1,458
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,300 reviews)
It was a good place to spend a staycation weekend. Well located and friendly staff

Reviewed on Mar 16, 2026

Ready to book your vacation to Bloomingdale?

 

Choose your dates

Bloomingdale Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $302 per night from Apr 12 to Apr 13
CA $302
CA $355 total
Apr 12 - Apr 13
includes taxes & fees
8.4/10 Very Good! (2,231 reviews)
Clean room and friendly staff

Reviewed on Mar 21, 2026

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is CA $174 per night from Mar 22 to Mar 23
CA $174
CA $198 total
Mar 22 - Mar 23
includes taxes & fees
8.8/10 Excellent! (2,424 reviews)
Great hotel!

Reviewed on Mar 20, 2026

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $184 per night from Apr 4 to Apr 5
CA $184
CA $216 total
Apr 4 - Apr 5
includes taxes & fees
8.6/10 Excellent! (1,234 reviews)
They have a shuttle to airport. Very nice hotel.

Reviewed on Mar 16, 2026

Marriott Chicago O'Hare
See all 1,896 properties in Bloomingdale
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Bloomingdale

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

4.5/5(19 reviews)

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
View of Chicago skyline at sunrise.

Naval Base Great Lakes

4.5/5(3 reviews)

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Naval Base Great Lakes

What to do in Bloomingdale

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $36
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
98% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in Bloomingdale

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.