A city skyline at dusk with illuminated buildings reflecting on the water.
Photo by Phil Ostroff
Open Photo by Phil Ostroff

Central Chicago Adventure Vacations

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

Top Adventure vacation packages in Central Chicago

Price found within the past 48 hours. Click for updated prices.
  • Dec 30 - Jan 2

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.4/10 - Very good (3,178 reviews)
    "Very clean. Had everything that we needed"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $948
    CA $737
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile
  • Jan 21 - Jan 24

    Sheraton Grand Chicago Riverwalk + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.6/10 - Excellent (1,880 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,107
    CA $794
    per traveller
    found 1 day ago
    Sheraton Grand Chicago Riverwalk
  • Jan 21 - Jan 24

    Park Hyatt Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,004 reviews)
    "This place was amazing and the hotel staff was extremely helpful"
    Reviewed November 10, 2026
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,801
    CA $1,316
    per traveller
    found 1 day ago
    Park Hyatt Chicago
  • Dec 30 - Jan 2

    The Talbott, Autograph Collection + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (198 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • Nonstop ORD - YTZ • Nonstop
    CA $1,026
    CA $792
    per traveller
    found 1 day ago
    The Talbott, Autograph Collection
  • Jan 21 - Jan 24

    Sofitel Chicago Magnificent Mile + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.4/10 - Exceptional (2,688 reviews)
    Roundtrip • Toronto (YTO) - Chicago (ORD)
    YTZ - ORD • 1 stop ORD - YYZ • Nonstop
    CA $1,176
    CA $923
    per traveller
    found 1 day ago
    Sofitel Chicago Magnificent Mile

Discover the most popular places to visit in Central Chicago

What to do in Central Chicago

Top Adventure Central Chicago Hotels

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 a Central Chicago vacation package cost?

Go from wondering to wandering with our Central Chicago vacation packages, which start from just CA $737. Pick the flights and hotels that match your travel plans. Then, add on some activities or tours for a one-of-a-kind escape.

How do I get a cheap travel package to Central Chicago?

Browse and lock in everything in one place with our Central Chicago vacation packages. You'll discover bargains on hotels, flights and more that'll keep your travel budget happy and your adventurous spirit full. And, with more than 550 air carriers and 1,000,000 hotels around the globe to choose from, you'll have endless opportunities to mix and match your own way.

Where should I stay in Central Chicago?

A journey to Central Chicago isn't complete without stopping by Wrigley Field and McCormick Place. Stay at a hotel nearby so you can easily access these terrific sights.

What are the top hotels in Central Chicago?

Hilton Garden Inn Chicago Central Loop and Kasa River North Chicago are among the most sought-after properties in Central Chicago. Why not have a look at the rates and facilities at each and then make a decision?

How far in advance should I book my Central Chicago vacation?

Search Expedia to compare international flights as early as possible. You can generally purchase a seat up to a year before departure. If you don't see your preferred carrier, or you've left things to the last moment, don't worry. Cheap fares to Central Chicago sometimes emerge a few weeks before the date of departure.

What does an Expedia Central Chicago travel package include?

Flights, car rentals and hotels — we connect you to the very best deals. All you'll have to do is pick your favorite combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to craft an exciting Central Chicago trip.

What should I know before booking a Central Chicago travel package?

You can save big by bundling your hotels, flights and rental cars. Once you've made your booking, you can add on tours and activities. Your next unforgettable vacation is only a couple of clicks away.

Can I choose my airline with a Central Chicago Expedia vacation package?

With a vacation package, the choice is in your hands. Whether you'd like to fly to Central Chicago in coach or first class, simply pick from the available airline options. Expedia has access to over 550 airline partners all over the world.

If I'm not able to travel, can I cancel my Central Chicago vacation package?

Because we understand life can be unpredictable, the answer is yes. For further details, visit our Customer Service Portal. But generally speaking, if you've booked your package in the last 24 hours, you may be able to cancel or change it with no penalties. Your airline, hotel or car rental company may charge a fee if you made your booking a while ago.