Bloomingdale Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

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 $976, price is now CA $604 per person
CA $604
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (343 reviews)
It was fine but nit as good as I had expected. Staff were un friendly and un helpful fur an expensive stay.

Reviewed on Aug. 27, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,883, price is now CA $1,120 per person
CA $1,120
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,064 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on Aug. 26, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $1,863, price is now CA $1,113 per person
CA $1,113
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
5 star hotel that goes above and beyond. My family loved staying at the Trump

Reviewed on Aug. 29, 2025

theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,022, price is now CA $654 per person
CA $654
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,007 reviews)
Very nice hotel and staff were pleasant. The area is okay but if you go a block over it is nicer. The river walk is very close and inviting.

Reviewed on Aug. 25, 2025

La Banque Hotel

La Banque Hotel

4 out of 5
Price was CA $1,638, price is now CA $1,054 per person
CA $1,054
per person
Nov 10 - Nov 17
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
9.4/10 Exceptional! (434 reviews)
Very nice hotel. Would definitely stay there again!

Reviewed on Aug. 26, 2025

Ready to book your vacation to Bloomingdale?

 

Choose your dates

Bloomingdale Hotel Deals

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 $209 per night from Sep 19 to Sep 20
CA $209
CA $246 total
Sep 19 - Sep 20
includes taxes & fees
Marriott Chicago O'Hare
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 $246 per night from Sep 19 to Sep 20
CA $246
CA $289 total
Sep 19 - Sep 20
includes taxes & fees
8.2/10 Very Good! (2,101 reviews)
Passing Thru
"Nice quiet and convenient hotel and room. Excellent staff."

Reviewed on Aug. 24, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from Sep 13 to Sep 14
CA $197
CA $224 total
Sep 13 - Sep 14
includes taxes & fees
8.6/10 Excellent! (1,896 reviews)
"Nice hotel to stay."

Reviewed on Aug. 25, 2025

Hyatt Regency O'Hare Chicago
See all 1,783 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

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

Wrigley Field
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

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
Navy Pier

Navy Pier

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

Navy Pier

What to do in Bloomingdale

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Bloomingdale

Frequently asked questions

How much does a Bloomingdale vacation package cost?
You'll find cheap prices from CA $604 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.