Explore the wonders of Chicago, a vibrant destination in Illinois. With 4,750 different vacation houses available, your dream vacation is within reach.
Find your perfect vacation houses in Chicago that fits both your style and budget. With prices ranging between $39 and $5,600, enjoy top-notch amenities like Internet / Wifi.
Top Features: Internet / Wifi, Air conditioner, TV, Kitchen / Kitchenette and Laundry
Local Highlights: Millennium Park, Navy Pier, Chicago Riverwalk, Museum of Science and Industry, Chicago and Museum Campus
Take the first step towards an unforgettable Chicago experience. Reserve your short term rentals today and uncover the hidden gems of Illinois.
Indulge in a peaceful retreat at Single Family Home! Sleeps 8 Lincoln Park/Lakeview, our elegant House in Chicago. Enjoy amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
Experience vacation in Chicago with our House, Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24. Enjoy amenities such as Air conditioner, Dishwasher and Fireplace, and more.
Experience vacation in Chicago with our House, The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence. Enjoy amenities such as Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.
Soak up the beauty of Chicago in our House, The Avondale Guesthouse. With a range of amenities such as Air conditioner, Fireplace and Internet / Wifi, you'll feel right at home.
Enjoy the best of Chicago in our House, Best Value, Quality Stay! Pets Allowed, Close to Chicago Riverwalk and The Cove. A stunning property with amenities including ;, and more.
Soak up the beauty of Chicago in our House, Amazing Lincoln Park Rowhouse - Perfect for Groups, Reunions and Cubs Games!. With a range of amenities such as Air conditioner, Dishwasher and Fireplace, you'll feel right at home.
Looking for a memorable stay in Chicago? Our House might just be what you're looking for. Enjoy amenities including Dishwasher, Fireplace and Internet / Wifi, and more during your stay.
When traveling to Chicago, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $1,150 per night.
Discover the beauty of Chicago with a stay at Updated Forest Park 3 BR Bungalow, a top rated House with amenities such as Air conditioner, Dishwasher and Internet / Wifi, and more.
Discover the beauty of Chicago with a stay at Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath, a top rated House with amenities such as Air conditioner, Dishwasher and Fireplace, and more.
This attractive House in Chicago, $839 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)
Experience vacation in Chicago with our House, Luxury Home Away From Your Home. Enjoy amenities such as Air conditioner, Internet / Wifi and Kitchen / Kitchenette, and more.
This House in Chicago, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!
Enjoy the best of Chicago in our House, The Wrigleyville VIP- 200 steps to Wrigley- Super Clean!. A stunning property with amenities including Air conditioner, Dishwasher and Internet / Wifi, and more.
Looking for a House in Chicago, this House for $150 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
When traveling to Chicago, if you are looking for (business stays, family stays, couples stay, getaway vacation, etc.) this is the perfect place at $105 per night.
House in Chicago, for $375 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
Business stays, family stays, couples stay, getaway vacation, and rental in Chicago at Griffin Mansion w/ Yard, 5 Mi to Dtwn Chicago! for $206 for your next trip.
Are you ready to indulge in a relaxing getaway? Our House in Chicago has everything you need for a rejuvenating stay. Treat yourself to Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location's exceptional amenities, such as Air conditioner, Dishwasher and Fireplace.
House in Chicago, for $759 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
Nestled in Chicago, this House is perfect for your next vacation. Enjoy Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars's top-rated amenities, including Air conditioner, Dishwasher and Fireplace, and more.
Looking for a House in Chicago, this House for $253 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.
House in Chicago, for $700 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)
This inviting House in Chicago can fit your needs for many types of vacations, at $649 per night.
This House in Chicago, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!