Bloomingdale Vacation Packages

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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.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,326, price is now CA $981 per person
CA $981
per person
Jul 17 - Jul 19
found 24 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too

Reviewed on May 3, 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 $1,683, price is now CA $1,142 per person
CA $1,142
per person
Jul 9 - Jul 12
found 19 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again

Reviewed on May 6, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $1,626, price is now CA $1,148 per person
CA $1,148
per person
Jun 30 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (2,144 reviews)
Keep an eye that nothing is added from the minibar but great property and can't wait to stay again!

Reviewed on May 5, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,677, price is now CA $1,251 per person
CA $1,251
per person
Jun 10 - Jun 13
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,122 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 2026

Cambria Hotel Chicago Loop - Theatre District

Cambria Hotel Chicago Loop - Theatre District

4 out of 5
Downtown Chicago
Price was CA $1,500, price is now CA $1,121 per person
CA $1,121
per person
Jun 30 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,578 reviews)
It was clean, the bed was amazing, the room was comfortable. the ground floor concierges/security were very knowledgeable and friendly.

Reviewed on May 4, 2026

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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 $230 per night from May 10 to May 11
CA $230
CA $263 total
May 10 - May 11
includes taxes & fees
8.8/10 Excellent! (2,539 reviews)
Well rested after my stay!

Reviewed on May 7, 2026

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 $339 per night from May 9 to May 10
CA $339
CA $399 total
May 9 - May 10
includes taxes & fees
8.4/10 Very Good! (2,282 reviews)
Wonderful location, staff were very helpful and room was clean. Older hotel but well maintained. Pricey but worthwhile for convenience sake.

Reviewed on May 5, 2026

Hilton Chicago O'Hare Airport
Comfort Suites Chicago O'Hare Airport

Comfort Suites Chicago O'Hare Airport

3 out of 5
4200 North River Road Schiller Park IL
Fully refundable
The price is CA $137 per night from May 25 to May 26
CA $137
CA $158 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (3,010 reviews)
Booked this hotel due to an early flight the next day. Exterior of the building was boarded up from a recent shooting. Inside needs a renovation. Couches in the rooms were ripped up, showers had visible mold, condom wrappers found in the room. Did not sleep in the bedding. Also this hotel is not ...

Reviewed on May 7, 2026

Comfort Suites Chicago O'Hare Airport
See all 1,925 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
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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
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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 $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Bloomingdale

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