Downtown Chicago vacation rentals
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Top-rated vacation rentals in Downtown Chicago
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Popular amenities for Downtown Chicago vacation rentals
Home rentals in Downtown Chicago
Home in Oak Park
4.88 out of 5 average rating, 104 reviewsUrban Chic 3beds w/2bath + free parking & W/D
Home in Chicago
4.95 out of 5 average rating, 38 reviewsGorgeous and Luxurious 3 BR Home
Home in Blue Island
4.81 out of 5 average rating, 182 reviewsWarm and comfortable inviting Suburban home !
Home in Des Plaines
4.73 out of 5 average rating, 89 reviewsHome for rent to traveling family and work.
Home in Justice
4.94 out of 5 average rating, 217 reviews3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin
Home in Chicago
4.98 out of 5 average rating, 43 reviews4BD/4BTH - Entire Building+Garage - Wicker Park!
Home in Prospect Heights
5 out of 5 average rating, 12 reviewsUpscale-5 Bed 4.5 Bath-3/4 Acre- 5400 sq ft
Home in Addison
4.95 out of 5 average rating, 57 reviewsHome in Unincorporated Addison. RV & Pet Friendly
Condo rentals in Downtown Chicago
Condo in Chicago
4.9 out of 5 average rating, 219 reviewsA Stones Throw from U Chicago South Campus!
Condo in Evergreen Park
4.8 out of 5 average rating, 109 reviewsEvergreen Park Condo with balcony and Jacuzzi tub
Condo in Chicago
4.95 out of 5 average rating, 118 reviewsEntire 3Bed/2Bath Condo Near McCormick & Metro
Condo in Chicago
4.9 out of 5 average rating, 101 reviewsConvenient & Spacious 3BR Condo w/Free Parking
Condo in Chicago
4.92 out of 5 average rating, 131 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Condo in Chicago
4.98 out of 5 average rating, 242 reviewsNear Lake Michigan & Wrigley Field
Condo in Chicago
5 out of 5 average rating, 135 reviewsSpacious 4 Bedroom Condo
Condo in Chicago
4.99 out of 5 average rating, 124 reviewsLuxurious River North 3BR/2BA- Free Onsite Parking
Apartment rentals in Downtown Chicago
Rental unit in Evanston
4.82 out of 5 average rating, 164 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Rental unit in Chicago
4.84 out of 5 average rating, 371 reviewsCozy Garden Unit In Edgewater
Rental unit in Chicago
4.86 out of 5 average rating, 508 reviewsLogan Square Lookout
Rental unit in Whiting
4.84 out of 5 average rating, 141 reviewsNEW! |Studio Apartment Whiting IN, United States#2
Rental unit in Chicago
4.99 out of 5 average rating, 180 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Rental unit in Chicago
4.97 out of 5 average rating, 132 reviewsInviting 2 Bedroom Apartment in Roscoe Village
Rental unit in Chicago
4.93 out of 5 average rating, 502 reviewsRestored Apartment in Historic Victorian Home
Rental unit in Chicago
4.82 out of 5 average rating, 243 reviewsBERNARD CHATEAU - LOGAN SQUARE
Frequently Asked Questions
How is the weather in Downtown Chicago?
Downtown Chicago experiences a diverse climate. Summers can be hot, typically reaching 85°F (29°C), while winter temperatures can drop to around 20°F (-6°C), often accompanied by snow. The transitional seasons, spring and fall, offer more moderate weather, making them pleasant times to visit.
What are some of the best things to do in Downtown Chicago?
There's no shortage of activities in Downtown Chicago. Explore the Art Institute of Chicago, walk alongside the Chicago River, or enjoy a stroll in Millennium Park. You can also marvel at the city's skyline from the Willis Tower's Skydeck or take a boat cruise on Lake Michigan.
What is the best time of year to visit Downtown Chicago?
The summer months, from June to August, are a great time to explore Downtown Chicago as the city comes alive with a range of cultural events including Lollapalooza, the Chicago Air and Water Show, and the Jazz Festival. However, the city also offers distinctive charm during the winter season, with events like the Magnificent Mile Lights Festival and the Winter WonderFest.
What are the best places to stay in Downtown Chicago?
Guests enjoy staying in several areas in Downtown Chicago. The Loop, Chicago's central business district, is known for its bustling atmosphere and close proximity to many attractions. River North, with its art galleries and fashion outlets, is also popular. Streeterville, near Navy Pier and Magnificent Mile, is another preferred location.
What are the best places to visit in Downtown Chicago?
There are many popular places to visit in Downtown Chicago. These include the Navy Pier, with its iconic Ferris wheel, the Art Institute of Chicago, known for its impressive collection, and the historic Chicago Theatre. Don't miss a walk down the Magnificent Mile for shopping and dining.
What are some hiking trails in Downtown Chicago?
While Downtown Chicago is primarily urban, there are lovely trails to explore. The 18-mile (29 km) Lakefront Trail along Lake Michigan is a favorite among locals and visitors. The Chicago Riverwalk also provides a scenic urban hike through the heart of the city.
What are some family activities to do in Downtown Chicago?
Families in Downtown Chicago can explore a multitude of engaging activities. Visit the Shedd Aquarium or the Field Museum for an educational outing, enjoy outdoor fun at Maggie Daley Park, or discover the wonders of space at the Adler Planetarium.
What are some of the best day trip ideas in Downtown Chicago?
For day trips, consider exploring the natural beauty of the Chicago Botanic Garden or the historical architecture in Oak Park, both within a short drive from Downtown. Alternatively, the Indiana Dunes National Park, 50 miles (80 km) away, offers an escape to nature.
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