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.
The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,740, price is now CA $1,285 per person
CA $1,285
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
Great location, great space in the rooms!!

Reviewed on Jun 21, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $3,802, price is now CA $2,621 per person
CA $2,621
per person
Aug 1 - Aug 5
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (498 reviews)
The place was serene,close proximity to Fulton market and had amazing views

Reviewed on Jun 22, 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 $2,442, price is now CA $1,689 per person
CA $1,689
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (2,557 reviews)
The hotel and location are beautiful but there needs to be much clearer signage as to where the entrance of the hotel is and the main lobby. Extremely confusing to travellers.

Reviewed on Jun 23, 2026

Level Chicago - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
Price was CA $2,376, price is now CA $1,714 per person
CA $1,714
per person
Aug 3 - Aug 7
found 11 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (1,034 reviews)
Really plan ahead when it comes to parking. You’ll get ticketed for just trying to put your things in your vehicle.

Reviewed on Jun 19, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $2,178, price is now CA $1,591 per person
CA $1,591
per person
Aug 26 - Sep 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
8.2/10 Very good! (2,767 reviews)
Overall, the hotel was okay for the price, but pretty basic. The room was very simple and lacked some expected amenities—there were no slippers provided, which was a bit disappointing. Also, the area around the bed wasn’t very clean, which affected the overall experience. I paid $170 per night, and for that price, I expected a bit more attention to cleanliness and comfort. It’s not terrible, but definitely not great either.

Reviewed on Jun 22, 2026

Ready to book your vacation to Bloomingdale?

 

Choose your dates

Bloomingdale Hotel Deals

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 CA $180 per night from Jun 28 to Jun 29
CA $180
CA $205 total
Jun 28 - Jun 29
includes taxes & fees
Hyatt Regency O'Hare Chicago
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 $359 per night from Jul 3 to Jul 4
CA $359
CA $422 total
Jul 3 - Jul 4
includes taxes & fees
8.4/10 Very good! (2,323 reviews)
"I love how convenient this hotel is. However they should FIRE their designer. Whoever thought shag carpets work with rolling luggage has never been a guest at the hotel. The room hallways have a lower profile carpet but still difficult. Even the maintenance people joke about it; not really funny ..."

Reviewed on Jun 22, 2026

Hilton Chicago O'Hare Airport
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
Fully refundable
The price is CA $187 per night from Jun 28 to Jun 29
CA $187
CA $215 total
Jun 28 - Jun 29
includes taxes & fees
9/10 Wonderful! (3,006 reviews)
"Friendly staff, clean facilities."

Reviewed on Jun 23, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
See all 1,844 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

Wrigley Field

4.5/5(159 reviews)

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

Wrigley Field
A coastal cityscape with high-rise buildings, a marina, and a park area.

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
Navy Pier

Navy Pier

4.5/5(460 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Bloomingdale

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River and Lake Cruise

CA $69
per adult
94% of travellers recommend
Chicago By Night River and Lake Cruise
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.