Streamwood Vacation Packages
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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.
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,161, price is now CA $787 per person
CA $787
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (116 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.
Reviewed on May 17, 2026
Level Chicago Fulton Market
Downtown Chicago
Price was CA $2,919, price is now CA $1,699 per person
CA $1,699
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.
Reviewed on May 22, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,741, price is now CA $1,702 per person
CA $1,702
per person
Aug 2 - Aug 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
JW Marriott Chicago
Downtown Chicago
Price was CA $1,405, price is now CA $950 per person
CA $950
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,000 reviews)
Good location close to many attractions like sears tower, the bean, river boat tours... nuce rooms ... public parking 1/2 block from premises .. just an overal great property with excellent convenience for tourists type activities
Reviewed on May 3, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,495, price is now CA $1,049 per person
CA $1,049
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Great views of the lake, staff very helpful the rooms were clean and comfortable. Would stay there again!
Reviewed on May 26, 2026
Streamwood Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $392 per night from May 29 to May 30
CA $392
CA $460 total
May 29 - May 30
includes taxes & fees
8.4/10 Very Good! (2,309 reviews)
"Conveniently located near Terminal 1 and 2 at OHare; staff extremely kind and helpful. Food available inside hotel until 12 midnight."
Reviewed on May 25, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $233 per night from May 28 to May 29
CA $233
CA $266 total
May 28 - May 29
includes taxes & fees
8.8/10 Excellent! (2,576 reviews)
"Everything is perfect. Clean room, clean hotel and safe too."
Reviewed on May 26, 2026
Holiday Inn Chicago O'Hare – Rosemont by IHG
6600 Mannheim Road, building 2 Rosemont IL
Fully refundable
The price is CA $186 per night from Jun 21 to Jun 22
CA $186
CA $215 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (2,968 reviews)
"We love staying here when we have an early morning flight out of Chicago O’Hare airport. Having the restaurant right there is wonderful so you don’t have to leave the hotel to grab a bite. We have eaten there for dinners and the food has been really good."
Reviewed on May 26, 2026
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.
Discover the most popular places to visit in Streamwood
Wrigley Field
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Streamwood
Skydeck - Willis Tower Admission
CA $60
per adult
96% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
