Chicago Vacation Rentals
Check Chicago vacation rental availability
Vacation Rentals in Chicago
51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi
LakeHouse
4-Bedroom Penthouse w/ 2 Large Balconies & Rooftop
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
Vintage Graystone in Little Italy near the loop UIC United Ct & McCormick Place
The Neighborhood Hotel-Little Italy
Walking distance to restaurants, shops and Lake Michigan,
Wrigley/Southport Corridor Garden Oasis +parking!
Kasa River North Chicago
Brand new entire 3 bedroom unit. 7 miles from dwntwn, 4 miles frm United Center
Beautiful, Remodeled Penthouse Unit in Old Town!
Cozy modern unit w/ easy access to downtown Chi
Kasa South Loop Chicago
national historic home near downtown airports no parties no events
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Sentral Michigan Avenue
Kasa Magnificent Mile Chicago
Home Away from Home! Budget-friendly Accommodation! Pets Allowed, Pool, Parking
Sonder The Burnham
Luxury Home Away From Your Home
Chicago Vacation Rental Travel Info
Number of vacation rentals | 8 |
---|---|
Popular accommodation | Chicago apartments |
Known landmarks | Art Institute of Chicago, Chicago Riverwalk and Chicago Theatre |
International airports | Chicago, IL (ORD-O'Hare Intl.) and Chicago, IL (MDW-Midway Intl.) |
Price trends for vacation rentals in Chicago
Less expensive | More expensive | Next month |
---|---|---|
April | July | $276 |
Month | Price |
---|---|
January | $115 |
February | $120 |
March | $115 |
April | $113 |
May | $248 |
June | $276 |
July | $295 |
August | $290 |
September | $180 |
October | $190 |
November | $165 |
December | $151 |
Other types of properties in Chicago you may be interested in
River Hotel
The Westin Michigan Avenue Chicago
Warwick Allerton - Chicago
Everything you need to know about Chicago vacation rentals
Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chicago vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chicago vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Chicago vacation rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Chicago. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chicago in high season.
Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $72 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!
How to find incredible deals on Chicago rentals
At Expedia, we put the best Chicago vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Chicago rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chicago vacation.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chicago. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
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