A city skyline at night with reflections in the water.

Oak Brook 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 Oak Brook Vacation

Come and discover this fascinating city for yourself with a Oak Brook vacation package. Consider spending some time in the neighborhood of North Lawndale, which is great for golfing and walking, and your time here is bound to be unforgettable. Brookfield Zoo, Morton Arboretum and Oakbrook Center Mall are just some of the many attractions worth exploring during your trip to Oak Brook. Expedia will help you escape your routine. Tailor your vacation to Oak Brook to match your travel style, whatever that may look like.

Top Oak Brook vacation deals

Price found within the past 48 hours. Click for updated prices.
  • Dec 19 - Dec 23

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    4 nights
    4.0 star property
    8.6/10 - Excellent (1,876 reviews)
    Roundtrip • Hamilton (YHM) - Chicago (ORD)
    YHM - ORD • 1 stop ORD - YHM • 1 stop
    CA $2,739
    CA $1,191
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 17 - Jan 20

    The Peninsula Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.8/10 - Exceptional (1,008 reviews)
    Roundtrip • Calgary (YYC) - Chicago (ORD)
    YYC - ORD • 1 stop ORD - YYC • 1 stop
    CA $1,909
    CA $1,330
    per traveller
    found 1 day ago
    The Peninsula Chicago
  • Dec 27 - Jan 2

    Kimpton Gray Hotel by IHG + Flight

    Downtown Chicago
    6 nights
    4.5 star property
    9.4/10 - Exceptional (1,003 reviews)
    "Rooms were dated and carpeting was old. There was just a sense that it had seen better days. Beds were good. Would not stay in that neighborhood next time."
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    Save 100% on your flight
    CA $2,098
    CA $1,465
    per traveller
    found 1 day ago
    Kimpton Gray Hotel by IHG
  • Dec 27 - Jan 2

    Park Hyatt Chicago + Flight

    Downtown Chicago
    6 nights
    5.0 star property
    9.6/10 - Exceptional (1,001 reviews)
    "Given the price point and other reviews, we came here expecting a luxury stay similar to the Waldorf Astoria, Four Seasons, and Peninsula, which are some of our favorite properties to stay at. However, everything from the service and cleanliness to the ambiance of the entrance and lobby and the amenities (other than the gym, which was excellent) is best described as an upgraded version of an average Hilton, Hyatt, or Marriott. For example, there was a hair in the bed. When we reported it, the..."
    Reviewed November 4, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    Save 100% on your flight
    CA $3,612
    CA $2,536
    per traveller
    found 1 day ago
    Park Hyatt Chicago
  • Dec 24 - Dec 28

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    4 nights
    5.0 star property
    9.6/10 - Exceptional (2,077 reviews)
    "Beautiful hotel situated perfectly for most downtown Chicago activities. Attentive staff and amazing views from our 14th floor lake view room. This stay has been on my bucket list for awhile. This hotel experience did not disappoint"
    Reviewed November 6, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $2,457
    CA $1,902
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago

Discover the most popular places to visit in Oak Brook

What to do in Oak Brook

Oak Brook Hotel Deals

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.

Frequently Asked Questions

How much does an Oak Brook vacation package cost?

You'll find cheap prices from CA $1,191 on Expedia for your Oak Brook break. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Oak Brook costs.

What are the cheapest months to go to Oak Brook?

January, February and April are great times to search for cheap Oak Brook vacation packages. Opting to travel in quieter months means you can typically find lower prices on hotels and flights.

How many days is enough for Oak Brook?

Dedicate around 2 days for your Oak Brook vacation to take in everything that makes this place unique. Explore key neighbourhoods, including Yorkfield and York Centre. Then check out top attractions like Yorktown Shopping Centre and Galloping Ghost. With a well-organized itinerary, you'll be kept busy with room for some relaxation too. Want to venture outside of Oak Brook? Consider fitting in a day trip or two.

Is it worth booking a vacation package to Oak Brook?

Boasting a host of highlights starting with its top-notch golfing, Oak Brook is a good vacation destination. Whether you'd like to check out attractions like Mayslake Peabody Mansion and Lizzadro Museum of Lapidary Art or take the road less travelled, you'll find plenty to keep you busy during your Oak Brook vacation.

How to find the best Oak Brook package deals?

Use Expedia's filter tool to find some tempting Oak Brook package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Oak Brook package deals in the off-peak season. Switch up your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.

Is it cheaper to book an Oak Brook vacation as a package?

You can enjoy significant savings on your next Oak Brook getaway by booking a tailored vacation package. Check the "Package" heading, then enter your travel dates and destination to see some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.

When to book a vacation package to Oak Brook?

If you're planning a spontaneous Oak Brook getaway, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.

How to plan a trip to Oak Brook?

  1. Pick your travel dates: The things you'd like to do in Oak Brook and your preferred season will help you decide when to travel.
  2. Set your budget: Factor in expenses like flights, food and transportation when calculating how much to put aside for your trip to Oak Brook. Then, choose a property that fits your budget, whether that's an economical stay or a more upscale retreat.
  3. Decide your trip length: Consider how long you'd like to spend discovering Oak Brook. Plan your days so you can get to all the activities and attractions you're interested in at a comfortable pace.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick an Oak Brook 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.