Brooklyn Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

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

Top Brooklyn 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 14 hours 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

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 14 hours 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 $1,106, price is now CA $794 per person
CA $794
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)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,801, price is now CA $1,315 per person
CA $1,315
per person
Jan 21 - Jan 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
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

Ready to book your vacation to Brooklyn?

 

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Brooklyn Hotel Deals

The Madison Concourse Hotel and Governor's Club

The Madison Concourse Hotel and Governor's Club

3.5 out of 5
1 W Dayton St Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $151 per night from Nov 17 to Nov 18
CA $151
CA $175 total
Nov 17 - Nov 18
includes taxes & fees
The Madison Concourse Hotel and Governor's Club
Motel 6 Madison, WI - East

Motel 6 Madison, WI - East

2 out of 5
4202 E Towne Blvd Madison WI
Fully refundable
The price is CA $75 per night from Dec 4 to Dec 5
CA $75
CA $86 total
Dec 4 - Dec 5
includes taxes & fees
6.2/10 (1,060 reviews)
":)"

Reviewed on Nov 9, 2026

Motel 6 Madison, WI - East
Baymont by Wyndham Madison West/Middleton WI West

Baymont by Wyndham Madison West/Middleton WI West

2.5 out of 5
8102 Excelsior Dr Madison WI
Fully refundableReserve now, pay when you stay
The price is CA $96 per night from Dec 2 to Dec 3
CA $96
CA $111 total
Dec 2 - Dec 3
includes taxes & fees
Baymont by Wyndham Madison West/Middleton WI West
See all 493 properties in Brooklyn
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

Frequently asked questions

How much does a Brooklyn vacation package cost?
You'll find cheap prices from CA $671 on Expedia for your Brooklyn break. However, factors like the length of stay, hotel choice and season will determine how much your vacation to Brooklyn costs.
What are the cheapest months to go to Brooklyn?
If you'd like to book a cheap Brooklyn vacation package, consider travelling in January, February and November. You'll generally find lower prices on flights and accommodations during these quieter months — perfect for a budget-friendly break.
How many days is enough for Brooklyn?
The ideal length for your Brooklyn vacation depends on what you'd like to see. Typically, a few days to a week will give you enough time to hit all the major attractions and explore some hidden gems along the way.
How to find the best Brooklyn package deals?
Start your search for a Brooklyn package deal by entering your travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with big savings. If you don't find the perfect Brooklyn package deal right away, simply switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Brooklyn escape underway.
Is it cheaper to book a Brooklyn vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still enjoy the freedom to create a tailored Brooklyn vacation by choosing your favourite type of stay, airline and car class.
When to book a vacation package to Brooklyn?
If you've got your Brooklyn travel dates finalized, book as soon as you can to score some outstanding deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous adventures? Our last-minute deals are great for jetting off on a whim.
How to plan a trip to Brooklyn?

  1. Choose your travel dates: The things you plan to do in Brooklyn and your preferred season will help you decide when to get away.
  2. Set your budget: Factor in costs like flights, meals and transportation when working out how much to save for your trip to Brooklyn. Then, select a hotel that fits your budget, whether that's an affordable option or a more luxurious getaway.
  3. Decide your trip length: Think about how long you want to spend exploring Brooklyn. Plan your itinerary so you can get to all the experiences and attractions you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in place, you can combine your hotels, car rental, flights and more into a customized Brooklyn vacation package.

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