Streamwood 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

Your Streamwood Vacation

Prepare to experience Streamwood on your terms with a custom Streamwood vacation package! Discovering the treasures of this city is made simpler with a base in a neighborhood such as Medinah, which is great for golfing, among many other things. You'll want to do some exploring during your trip to Streamwood. Make time for popular attractions like Schaumburg Medieval Times, Grand Victoria Casino and Santas Village. Your dream Streamwood vacation is just a few clicks away. Search hotels, flights and more on Expedia for a trip that's tailored to suit your travel style.

Top Streamwood Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was CA $1,256, price is now CA $866 per person
CA $866
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
Really small room. Outside windows need cleaned. Nice staff

Reviewed on Jun 30, 2026

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,665, price is now CA $1,162 per person
CA $1,162
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
The Pendry is in the heart of everything downtown. The blue line in from the airport was about a 7 minute walk from the lake stop. Rooftop bar is a nice visit as well as the lobby bar. Great staff, good vibes.

Reviewed on Jun 29, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,382, price is now CA $1,700 per person
CA $1,700
per person
Sep 1 - Sep 6
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well

Reviewed on Jun 26, 2026

Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,403, price is now CA $1,007 per person
CA $1,007
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Staff was extremely friendly and helpful! Very clean and inviting environment!

Reviewed on Jun 29, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,635, price is now CA $1,189 per person
CA $1,189
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,330 reviews)
Clean rooms, great location, helpful staff

Reviewed on Jun 29, 2026

Ready to book your vacation to Streamwood?

 

Choose your dates

Streamwood Hotel Deals

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
The price is CA $204 per night from Jul 5 to Jul 6
CA $204
CA $233 total
Jul 5 - Jul 6
includes taxes & fees
8.8/10 Excellent! (2,752 reviews)
"Location close to airport"

Reviewed on Jun 29, 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 $352 per night from Jul 3 to Jul 4
CA $352
CA $413 total
Jul 3 - Jul 4
includes taxes & fees
8.4/10 Very good! (2,328 reviews)
"Very close to airport"

Reviewed on Jun 29, 2026

Hilton Chicago O'Hare Airport
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 $240 per night from Jul 2 to Jul 3
CA $240
CA $282 total
Jul 2 - Jul 3
includes taxes & fees
8.6/10 Excellent! (1,302 reviews)
"There are no microwaves in the rooms. You have to pay for parking. But everything else was exceptional!"

Reviewed on Jun 29, 2026

Marriott Chicago O'Hare
See all 1,128 properties in Streamwood
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

What to do in Streamwood

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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 all activities in Streamwood

Frequently asked questions

How much does a Streamwood vacation package cost?
You can pick up a vacation package to this destination from CA $866 on Expedia. But how much your vacation to Streamwood costs will depend on factors like the length of stay, hotel choice and season.
What are the cheapest months to go to Streamwood?
The off-season is the best time to visit Streamwood if you're trying to save. Another tip for scoring cheap Streamwood vacation packages? Avoid visiting during public holidays and any major festivals or events.
How many days is enough for Streamwood?
Generally, a few days is ideal for a Streamwood vacation. With a well-organized schedule, you can visit all the popular attractions like NOW Arena, as well as explore some hidden gems along the way.
How to find the best Streamwood package deals?
Use Expedia's filter tool to help you find some terrific Streamwood package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your adventure for midweek, or search for Streamwood package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Streamwood vacation as a package?
You can enjoy significant savings on your Streamwood escape by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to see the best airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Streamwood?
Score incredible bargains by booking your flights ahead of time with Expedia. If being spontaneous is more your style, take advantage of our last-minute deals for an impromptu Streamwood break.
How to plan a trip to Streamwood?

  1. Pick your dates: What you want to do in Streamwood and your favourite season can help you decide when to travel.
  2. Calculate your budget: Ensure you have enough money to pay for everything from dining out and transportation to experiences and flights. Your accommodations will probably be the biggest expense during your trip to Streamwood.
  3. Work out your trip length: Think about how much time you'd like to spend discovering Streamwood. Plan your days so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to pick a Streamwood vacation package that brings all your bookings together.

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.