Streamwood Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
Nice room and view. Rooftop was gorgeous

Reviewed on Jul. 13, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,006 reviews)
Nice property, very walkable. Front desk was great. Bar area nice & welcome drink nice. Concierge was not around. Got suite with 2 full baths which was awesome with teens. Great stay overall!

Reviewed on Jul. 12, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Great views, great service, great location

Reviewed on Jul. 13, 2025

Virgin Hotels Chicago

Virgin Hotels Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Sep 25 - Sep 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,334 reviews)
I love Virgin air and expected a 5-star experience. Hotel checkin was not all that welcoming, but efficientl. They had no valet service and basically told us we were on our own. Thought ok I need a drink so went to the rooftop bar. An afterthought at this hotel. Cushions were dirty and faded. Barely staffed. More like a rooftop bar in costs rica than downtown Chicago. Room was nice and stylish. The highlight of the stay tbh as was the coffee shop.

Reviewed on Jul. 13, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 16 - Aug 19
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Superb customer service, clean hotel!

Reviewed on Jun. 13, 2025

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
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from Jul 21 to Jul 22
CA $208
CA $237 total
Jul 21 - Jul 22
includes taxes & fees
8.6/10 Excellent! (1,729 reviews)
"This was a last minute booking as our flight got cancelled. Airport shuttle was a life saver!!"

Reviewed on Jul. 12, 2025

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 $245 per night from Aug 8 to Aug 9
CA $245
CA $288 total
Aug 8 - Aug 9
includes taxes & fees
8/10 Very Good! (2,077 reviews)
Convenient location
"Excellent option when traveling from ORD. Convenient location with direct access to the airport terminal. Good facilities."

Reviewed on Jul. 13, 2025

Hilton Chicago O'Hare Airport
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
3.5 out of 5
5440 N River Rd, Rosemont, IL
Fully refundable
The price is CA $179 per night from Aug 10 to Aug 11
CA $179
CA $204 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (2,289 reviews)
"It was a very nice hotel very clean and friendly atmosphere"

Reviewed on Jul. 12, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
See all 1,080 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

Discover the most popular places to visit in Streamwood

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
Navy Pier

Navy Pier

4.5/5(459 reviews)

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

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

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

What to do in Streamwood

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
94% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
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 $61
per adult
92% of travellers recommend
Chicago By Night River & Lake Cruise
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 $615 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.

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