Medinah Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Your Medinah Vacation
Entertainment, history, art and more … There's so much to immerse yourself in with a Medinah vacation package. And with the ability to easily customize your city adventure, you know it'll be one you won't forget. If your trip to Medinah includes a little sightseeing, visit major attractions such as Woodfield Mall, Schaumburg Medieval Times and LEGOLAND® Discovery Center. A couple of clicks is all it takes to put together a customized Medinah vacation on Expedia.
Top Medinah Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
CA $1,290
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (4,907 reviews)
Room was very clean and spacious. Staff was very helpful when we had issues with wifi (which were resolved very fast) and issues with flight cancellations impacting our arrival. Great breakfast buffet, lots of options and convenient. Rooftop bar was beautiful! The location was perfect for walking around the city and for getting to the red line. Would definitely recommend!!
Reviewed on Aug 19, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
CA $1,262
per person
Oct 21 - Oct 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
Loved the location. Was able to park in the parking ramp, leave the car, and walk to many, many places! Room was clean, view was excellent, and choices of food/snacks was endless!
Reviewed on Aug 18, 2026
Ready to book your vacation to Medinah?
Medinah Hotel Deals
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
CA $188
CA $214 total
Aug 30 - Aug 31
includes taxes & fees
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $332
CA $390 total
Sep 12 - Sep 13
includes taxes & fees
8.4/10 Very good! (2,423 reviews)
"Easy access to early am flight!"
Reviewed on Aug 19, 2026
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
5440 N River Rd Rosemont IL
Fully refundable
CA $224
CA $255 total
Aug 23 - Aug 24
includes taxes & fees
8.6/10 Excellent! (2,950 reviews)
"Wonderful stay, right across from the convention center"
Reviewed on Aug 18, 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.
What to do in Medinah
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Medinah vacation package cost?
Offering great value package deals from CA $1,169 on Expedia, you'll be thrilled with how little a vacation to Medinah costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Medinah?
January, February and November are the best times to look for cheap Medinah vacation packages. Opting to travel in less busy periods means you can generally find better prices on hotels and flights.
How many days is enough for Medinah?
The ideal length for your Medinah vacation depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to hit all the leading sights and discover some hidden spots along the way.
How to find the best Medinah package deals?
Landing a cheap Medinah package deal is a cinch with Expedia. Once you've entered your destination and travel dates under our "Packages" tab, set your budget, add some filters and browse what's available. You can personalize your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Medinah package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are generally lower.
Is it cheaper to book a Medinah vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, hotel and car rental into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component individually. And you'll still get the freedom to create a customized Medinah vacation by choosing your favourite accommodation type, airline and car class.
When to book a vacation package to Medinah?
If you have your Medinah vacation dates finalized, book as early as you can to bag some fantastic deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are perfect for impromptu escapes.
How to plan a trip to Medinah?
- Pick the perfect time to travel: Your schedule, favourite season and the type of weather you enjoy can all impact your decision on when to go to Medinah.
- Set your budget: Factor in costs like flights, food and transportation when calculating how much to put aside for your trip to Medinah. Then, select a hotel that works with your budget, whether that's an affordable stay or a high-end retreat.
- Decide how long to go away for: Now that you know more about Medinah, you can work out the perfect length of your vacation. Create a rough itinerary and allocate enough time to get through everything on your must-do list.
- Bundle your airfare and accommodations: Once you've settled on your dates and duration, lock in the perfect Medinah vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
