Chicago Vacation Rentals

40 Rentals

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Chicago Illinois Vacation Rentals - Apartment

1BR / 1BA - Sleeps 3 - Chicago Apartment

These Vacation Rentals are located in the Chicago LOOP, a mixed- use neighborhood west of Michigan Avenue...

$89 - $220 / nt

5 Reviews

1BR / 1BA - Sleeps 3 - Chicago Apartment

Located in the heart of Chicago, these Corporate Furnished Apartments offer breathtaking views, rooftop...

$100 - $180 / nt

8 Reviews
Chicago Illinois Vacation Rentals - Apartment

2BR / 1BA - Sleeps 5 - Chicago Apartment

This lovely 2 Bedroom sits in the Downtown/Gold Coast area. Voted in the top 5 areas that are 'walkable'...

$200 - $250 / nt


5BR / 2BA - Sleeps 16 - Chicago Condo

Chicago Vacation Rental lenience # 2320200 This well kept property sleeps 14 comfortably with space...

$600 - $1,200 / nt

3 Reviews

4BR / 4BA - Sleeps 14 - Chicago Condo

A total of 4 bedroom 4 bath brand new construction luxury condos. We are a licensed vacation rental property...

$295 - $695 / nt

Chicago Illinois Vacation Rentals - Apartment

Studio / 1BA - Sleeps 2 - Chicago Apartment

Corporate furnished apartment in the heart of Millennium Park, walking distance to transportation,...

$99 - $149 / nt

10BR / 8BA - Sleeps 20 - Chicago Condo

Independent Bedroom Close to Downtown Chicago 18th dorm is located on heart of Pilsen. the six corner...

$50 - $60 / nt

2BR / 2BA - Sleeps 4 - Chicago Condo

, overlooking city, Lake Michigan and the Chicago River. Fully furnished 2 bedroom/2 bath. Building...

11 Reviews
Chicago Illinois Vacation Rentals - Townhouse

3BR / 2BA - Sleeps 8 - Chicago Townhouse

Gorgeous, Luxury Oak Park area Townhome…corner unit…completely furnished…. close proximity (2...

$300 - $450 / nt

Chicago Illinois Vacation Rentals - Condo

1BR / 1BA - Sleeps 4 - Chicago Condo

Experience the vibrancy of down town Chicago and delight in the modern, sleek comfort of wyndham grand...

$270 - $340 / nt


4BR / 3.5BA - Sleeps 24 - Chicago Home

Vacation in the best neighborhood in Chicago in this amazing Furnished Custom Single Family Home. This...

$500 - $1,150 / nt

6 Reviews

3BR / 2BA - Sleeps 6 - Chicago Condo

Beautifully done high- end furnished 3 bedroom | 2 bath | located downtown Chicago...

$400 / nt

Chicago Illinois Vacation Rentals - Guesthouse

5BR / 2BA - Sleeps 9 - Chicago Guesthouse

Whether you are coming to Chicago for work or play (or both) Chicago Guest House is the absolute BEST...

$399 - $499 / nt

3 Reviews
Hot Tub / Jacuzzi

1BR / 1.5BA - Sleeps 4 - Chicago Condo

If you're looking for a quiet and quaint stay in Chicago that is minutes away from all of the downtown...

$145 - $225 / nt

11 Reviews
Living room

1BR / 1BA - Sleeps 4 - Chicago Condo

Are you planning a trip to Chicago? Why stay in an expensive hotel room when you can rent furnished luxury...

$149 - $250 / nt

6 Reviews
Chicago Illinois Vacation Rentals - Condo

4BR / 2BA - Sleeps 8 - Chicago Condo

Brand new 4 bedroom 2 bath fully furnished apartment in the heart of Roscoe Village. Whether you’re...

$300 / nt

2 Reviews
Living Area with Queen Pull-Out Sofa

Studio / 1BA - Sleeps 2 - Chicago Apartment

Note: 30 Night Minimum Stay 215 W. Washington St. Chicago, IL. 60606 (Washington/Wells in the Loop...

$89 - $109 / nt

Unit 1: Living Room

3BR / 1BA - Sleeps 7 - Chicago Condo

Features 2 "independent" self catering units in the same building with fully functional kitchens. Coffee,...

$225 - $250 / nt

8 Reviews
Chicago Illinois Vacation Rentals - Condo

3BR / 2BA - Sleeps 8 - Chicago Condo

Accommodation Duplex, 3 Bedroom 2 Baths Sleeps (8- 10) Welcome to Roscoe Village Duplex Located in...

Chicago Illinois Vacation Rentals - Condo

3BR / 1BA - Sleeps 8 - Chicago Condo

Victorian 1500 sq ft. beautiful unit is in the heart of Lincoln Park. Live like a Chicago local in our...

2 Reviews

Chicago, Illinois Travel Tips

Chicago, the biggest metropolitan city in the Midwest, teems with rich culture, an eclectic art scene, exciting nightlife, die-hard sports fans, and of course, deep-dish pizza. This city isn't just a great travel destination for adults; it also has much to offer families and kids of all ages. If you have started to look for Chicago condo rentals for your upcoming family vacation, be sure to check out the following travel tips that will help you and your family enjoy your time in the "Windy City".
Admire the Awesome Animal Life
Chicago is a fun destination for are animal-lovers of any size. With all of its entertainment options and aquatic life, a visit to The John G. Shedd Aquarium can fill up an entire day. From dolphin shows to a 400,000-gallon underground shark tank, the Shedd Aquarium is a fun outing for the whole family. Try to buy your tickets for the aquarium online, as this can save you both time and money the day of your trip. For families looking to save some money on attractions, a trip to the Lincoln Park Zoo is a must, as kids will enjoy watching the animals and parents will appreciate the free admission.
Enjoy a Day at the Museum
Chicago is home to several world-class museums, including many that will excite the kids. For dinosaur enthusiasts, don't miss the Field Museum, which is home to the largest tyrannosaurus rex skeleton ever uncovered. Other great museums for children include the LEGO Discovery Center, the Museum of Science and Industry, and the Children's Museum. If you wish to be in walking distance of certain museums, make sure to keep that in mind while searching through the Chicago condo rentals for your trip - it's all about location, location, location - especially for busy families.
Ride the attractions at Navy Pier
As one of the most popular attractions in Chicago, Navy Pier is a great place for both children and adults. There are many Chicago condos for rent that are perfectly located for easy access to the Navy Pier, which offers carnival-like rides, boat rides, a Ferris wheel, fun restaurants, and many more family-oriented attractions. If you plan on spending a significant amount of time at Navy Pier, check to see if there are any Chicago vacation rentals by owner that are within walking distance of this hot spot.
Easy and Unique Public Transportation
Chicago has one of the best public transportation systems in the country, which can be extremely beneficial for visitors, especially those traveling with children. Not only is public transportation inexpensive, but kids can also experience riding the L-train - the elevated train that provides great views of downtown Chicago. If you plan on taking public transportation during your trip, choose from our selection of Chicago condos for rent close to a train station or bus stop.
If you are trying to find the perfect family vacation destination that offers a wide variety of options for condo rentals, Chicago is a great choice! Searching for condo rentals doesn't need to be challenging; we're here to help you find a place that fits all of your family's needs and aim to help you plan a memorable and comfortable family vacation. We provide a variety of vacation rentals by owner, Chicago and surrounding areas. With these affordable and fitting accommodations, Chicago might just be your new favorite family vacation spot.
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