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Discover a vacation rental fitting your needs among the 9,303 beautiful properties from more than 22 partner websites in Chicago. Using HomeToGo you can instantly search and compare the offers of each listed rental to find the best price and save up to 53%.
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More than a quarter of the accommodations provide a pool, which makes Chicago a wonderful destination for vacationers looking to relax pool-side. In addition, more Apartment rental have pools than any other type of property. They are an excellent choice if you go in a group of 8, as that is the number of people they can welcome on average. If you would ideally like to be close to the water, two-thirds of the vacation rentals with a pool are located within 2 miles of the waterfront.
We analyzed price data and input them into this graph, which displays vacation rental prices for the next twelve months in Chicago. In July, prices go up to $531 per night (7/19 – 7/26), which is the most expensive time of the year to book a vacation home. Vacation rental prices go down to $251 per night in January (1/4 – 1/11).
Check out the graph above to learn about the percentage accommodations are available in Chicago throughout the year. It is harder to find an accommodation during a week of August (8/9 – 8/16), as 93% of the rentals are booked. It is easier to find a rental in a week of October (10/26 – 11/2), as only 30% of the accommodations are booked.
Chicago's international neighborhoods are so true-to-life, you'd be forgiven for thinking you were genuinely in another country. There's Chinatown, the Korean community in Lawrence Avenue, the Swedish settlement at Andersonville, Little Italy, Greektown, and several other international pockets. The Polish Cathedrals of St. Mary of the Angels in Bucktown and St. Hyacinth Basilica in Avondale are exquisite. Experience the different facets of the city with guided architecture walks or a river boat tour.
The world comes to Chicago for gastronomical expertise, so indulge those taste buds! Devon Avenue is the place for Indian delights, and a mix of everything is served in Uptown, including American, Ghanaian, Nigerian, Japanese, and even Swedish delicacies.
Chicago is a drinking city that is home to a record number of dive bars, lounges, and breweries, the best of them found in the Logan Square and Bucktown areas.
The city’s location makes it convenient to explore neighboring destinations on short day trips. Just a 90-minute drive will take you to Milwaukee, a city known for its breweries. The Milwaukee Public Museum, Discovery World, and Harley-Davidson Museum are popular attractions in this Wisconsin city.
Get more out of your stay at a Chicago vacation house with a trip to Starved Rock State Park. A delight for outdoor enthusiasts, this park is known for the many sandstone canyons that were created by glacial meltwater. Explore the different hiking trails through lush green areas and spend time by the waterfalls.
Another worthwhile trip is to Michigan City, just an hour away from Chicago. Spend the day visiting popular attractions like Washington Park, the Old Lighthouse Museum, and the gorgeous Barker Mansion. Family vacationers can visit the zoo and later hit the beach area for some boating, surfing, and swimming.
1. 360 Chicago Observation Deck
What better to way to see the city than from above? Travel up to the 94th floor of the John Hancock Center for stunning views of the city and over Lake Michigan.
2. Lincoln Park Zoo
The city's most popular attraction, this iconic zoo houses African apes and other interesting species. Be sure to allow for plenty of time to explore its plentiful and varied exhibits!
3. Museum of Science and Industry
At this world-class interactive museum, you'll find a life-size replica coal mine and recreated historic Chicago streets, with functional shops and other interesting querks.
4. Cloud Gate
One of the most iconic pieces of art in the United States, Cloud Gate was created by Anish Kapoor. This beautiful reflective sculpture is nicknamed 'The Bean' due to its shape, and attracts photographers from across the world.
5. Millennium Park
This majestic urban park in the center of Chicago is a great place to wile away an afternoon amidst a tranquil backdrop. Concerts, local fairs, and fun events are held regularly at the park.
6. Art Institute of Chicago
As one of the oldest and largest galleries in the country, this impressive museum showcases over 300,000 artworks. Modern art, photography, and ancient sculptures are all on display for visitors to enjoy.
| 🏡 Vacation rentals available | 9,251 rentals |
|---|---|
| 💳 Possible discounts | up to 49% |
| 🌙 Nightly prices starting at | $25 |
| ⭐ Popular amenities | Internet, Pool and Parking |
| 🐾 Pet friendly homes | 4,249 homes |
| 🏊 Vacation rentals with pools | 2,335 homes |
The nightly price of accommodations in Chicago starts at $25. Average prices for apartment rentals are $322 per night. House rentals in Chicago cost on average $626 per night.
Currently there are 9,251 rentals in Chicago to browse and rent for your upcoming trip.
Usually travelers search for Pool, Internet, and Parking when booking a vacation rental in Chicago.
There are 2,335 vacation rentals from 24 providers in Chicago.
If you are traveling with a dog in Chicago - 46% of vacation homes allow pets.
If you are booking a vacation home in Chicago, consider that rainy season is typically in March or April, with February often being the driest.