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.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,352, price is now CA $941 per person
CA $941
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,898, price is now CA $1,336 per person
CA $1,336
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,068, price is now CA $756 per person
CA $756
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

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 $1,284, price is now CA $938 per person
CA $938
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)
Everything was nice. The room was clean and a nice size but it’s the views that make it worthwhile! Waking up & seeing the beautiful sunrise over the lake was amazing!!

Reviewed on Nov 11, 2026

Ready to book your vacation to Bloomingdale?

 

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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 $258 per night from Dec 12 to Dec 13
CA $258
CA $303 total
Dec 12 - Dec 13
includes taxes & fees
Hilton Chicago O'Hare Airport
Chicago Club Inn & Suites

Chicago Club Inn & Suites

3 out of 5
630 Pasquinelli Dr Westmont IL
Fully refundableReserve now, pay when you stay
The price is CA $90 per night from Dec 10 to Dec 11
CA $90
CA $100 total
Dec 10 - Dec 11
includes taxes & fees
Chicago Club Inn & Suites
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 $202 per night from Nov 26 to Nov 27
CA $202
CA $237 total
Nov 26 - Nov 27
includes taxes & fees
Marriott Chicago O'Hare
See all 1,891 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.
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Stay near popular Bloomingdale attractions

Bloomingdale Golf Club

8.0/10 (12 reviews)
Enjoy a round of golf in Bloomingdale at Bloomingdale Golf Club. Attend a sporting event while in this family-friendly area or simply enjoy the top-notch restaurants.
See properties

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
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Bloomingdale

Frequently asked questions

How much does a Bloomingdale vacation package cost?
You'll find cheap prices from CA $671 on Expedia for your Bloomingdale getaway. However, factors like the season, choice of hotel and length of stay will influence how much your vacation to Bloomingdale costs.
What are the cheapest months to go to Bloomingdale?
You can typically find lower rates and better availability in February, April and October. Check out our cheap Bloomingdale vacation packages and you could score some great off-season deals.
How many days is enough for Bloomingdale?
Generally, a few days is great for a Bloomingdale vacation. With a detailed itinerary, you can visit all the main attractions such as The Oasis Water Park, as well as explore some hidden gems along the way.
Is it worth booking a vacation package to Bloomingdale?
Known for its golfing, nature and plenty of other highlights, you can be assured Bloomingdale is a good vacation destination. Some of the top attractions to put on your itinerary? Visit The Oasis Water Park and Bloomingdale Golf Club during your Bloomingdale vacation.
How to find the best Bloomingdale package deals?
Landing a cheap Bloomingdale package deal is a breeze with Expedia. Once you've entered your trip dates and destination under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Bloomingdale package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book a Bloomingdale vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll usually get a better deal than booking each component individually. And you'll still get the flexibility to create a customized Bloomingdale vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Bloomingdale?
Score incredible bargains by reserving your flights ahead of time with Expedia. If being spontaneous is more your thing, snap up one of our last-minute deals for an impromptu Bloomingdale break.
How to plan a trip to Bloomingdale?

  1. Choose your dates: What you want to do in Bloomingdale and your preferred season will help you decide when to get away.
  2. Plan your budget wisely: Besides the cost of your stay, you'll need to factor in other expenses. These include food, flights and transportation. Also, put aside a little extra for unexpected expenses that could arise during your trip to Bloomingdale.
  3. Determine how many days away: Start by listing all the sights and activities you want to experience in Bloomingdale. Then, estimate how long you'll need for each, along with any travel time.
  4. Combine your accommodations and airfare: Once you've settled on your trip dates and duration, lock in the ideal Bloomingdale vacation package for you.

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