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
Downtown Chicago apartment rentals
Rental unit in Chicago
4.95 out of 5 average rating, 109 reviewsElegant Depaul Apt on Jonquil Park
Rental unit in Evanston
4.84 out of 5 average rating, 240 reviewsAdorable 1BR apartment near Northwestern
Rental unit in Evanston
4.82 out of 5 average rating, 167 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private
Rental unit in Chicago
4.93 out of 5 average rating, 146 reviewsExecutive Apartment on Lake Michigan with parking
Rental unit in Chicago
4.99 out of 5 average rating, 182 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!
Rental unit in Chicago
4.97 out of 5 average rating, 135 reviewsInviting 2 Bedroom Apartment in Roscoe Village
Rental unit in Chicago
4.92 out of 5 average rating, 101 reviewsCitySlickers Crash Pad /Free Parking /No Clean Fee
Rental unit in Chicago
4.83 out of 5 average rating, 246 reviewsBERNARD CHATEAU - LOGAN SQUARE
Downtown Chicago condo rentals
Condo in Evergreen Park
4.8 out of 5 average rating, 110 reviewsEvergreen Park Condo with balcony and Jacuzzi tub
Condo in Chicago
4.9 out of 5 average rating, 220 reviewsA Stones Throw from U Chicago South Campus!
Condo in Chicago
4.95 out of 5 average rating, 118 reviewsEntire 3Bed/2Bath Condo Near McCormick & Metro
Condo in Chicago
4.89 out of 5 average rating, 104 reviewsConvenient & Spacious 3BR Condo w/Free Parking
Condo in Chicago
4.92 out of 5 average rating, 135 reviewsModern designed 2bed/2bath | Heart of Bronzeville!
Condo in Chicago
4.98 out of 5 average rating, 245 reviewsNear Lake Michigan & Wrigley Field
Condo in Chicago
4.99 out of 5 average rating, 124 reviewsLuxurious River North 3BR/2BA- Free Onsite Parking
Condo in Mount Prospect
4.9 out of 5 average rating, 180 reviewsLovely 3-bedroom condo, free parking, Unite 1
Other great vacation rentals in Downtown Chicago
Home in Chicago
4.92 out of 5 average rating, 24 reviewsFamily Friendly Duplex/9 min from MDW/Free Parking
Home in Elmhurst
4.91 out of 5 average rating, 11 reviewsEnamored in Elmhurst
Rental unit in Chicago
4.85 out of 5 average rating, 125 reviews3 BR condo with great views, free WIFI and parking
Rental unit in Chicago
4.94 out of 5 average rating, 34 reviewsElegant 4Bedroom with Free Parking in Albany Park
Rental unit in Chicago
4.9 out of 5 average rating, 10 reviewsCity Gem: Stylish 3BR for Urban Explorers
Condo in Chicago
4.79 out of 5 average rating, 28 reviewsSpacious condo with open floor plan and fireplace
Bungalow in Chicago
4.94 out of 5 average rating, 100 reviewsChicago Bootlegger House Sleeps 10-20
Rental unit in Forest Park
4.86 out of 5 average rating, 204 reviewsHome in Forest Park downstairs
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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