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.
  • A spacious lobby with a central seating area, a piano, and a large window overlooking a garden.
    Dec 30 - Jan 4

    Hyatt Regency Deerfield + Flight

    Deerfield
    5 nights
    4.0 star property
    8.8/10 - Excellent (1,343 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,042
    CA $810
    per traveller
    found 3 hours ago
    Hyatt Regency Deerfield
  • An outdoor seating area with a fire pit, wooden benches, and tables, surrounded by large windows and string lights.
    Dec 19 - Dec 25

    The Emily Hotel + Flight

    Downtown Chicago
    6 nights
    4.0 star property
    9.2/10 - Wonderful (1,360 reviews)
    "Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights."
    Reviewed November 13, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $1,734
    CA $1,159
    per traveller
    found 16 hours ago
    The Emily Hotel
  • A rooftop bar with seating and a view of the city skyline at night.
    Jan 29 - Feb 2

    The Peninsula Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.8/10 - Exceptional (1,000 reviews)
    Roundtrip • Toronto (YYZ) - Chicago (ORD)
    YYZ - ORD • Nonstop ORD - YYZ • Nonstop
    CA $2,282
    CA $1,610
    per traveller
    found 1 day ago
    The Peninsula Chicago
  • An outdoor seating area with a glass table, orange cushions, and potted plants.
    Dec 20 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,885 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,118
    CA $819
    per traveller
    found 23 hours ago
    Sheraton Grand Chicago Riverwalk
  • A modern bedroom with a large window, a bed, a nightstand, and a chair.
    Jan 24 - Jan 26

    Level Chicago - River North + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.2/10 - Wonderful (1,172 reviews)
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop MDW - YUL • 1 stop
    CA $1,217
    CA $920
    per traveller
    found 1 day ago
    Level Chicago - River North

Streamwood Hotel Deals

A modern hotel lobby with a reception desk, seating area, and a large flat-screen TV.

Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG

Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG
3.5 star property
5.6 km from Streamwood
9.2 out of 10, Wonderful, (849 reviews)
The price is CA $145
CA $164 total
includes taxes & fees
Dec 14 - Dec 15
Holiday Inn Express & Suites Chicago - Hoffman Estates by IHG
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.
See all properties 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 $810 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.