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
Apartment in Cicero
4.98 out of 5 average rating, 208 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Apartment in West Town
4.92 out of 5 average rating, 331 reviewsBright, Modern Apartment in a Vintage Greystone
Apartment in Chicago
4.89 out of 5 average rating, 143 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Apartment in East Rogers Park
4.89 out of 5 average rating, 107 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 249 reviewsModern
Apartment in Chicago
4.96 out of 5 average rating, 266 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Apartment in Chicago
4.96 out of 5 average rating, 246 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Apartment in Andersonville
4.82 out of 5 average rating, 442 reviewsLovely Andersonville Apt with Ideal Location
Downtown Chicago condo rentals
Condo in West Town
4.86 out of 5 average rating, 196 reviewsBold Ukrainian Village 2 Bedroom w/Garage Parking
Condo in West Town
4.87 out of 5 average rating, 110 reviewsSpacious Duplex in Great Location
Condo in Lincoln Park
4.96 out of 5 average rating, 446 reviewsUnique Lincoln Park Duplex Apt
Condo in Lake View
4.99 out of 5 average rating, 573 reviewsUrban Comfort in the Heart of Chicago
Condo in Chicago
4.87 out of 5 average rating, 129 reviews3D Tour! Designer Condo near Logan Square
Condo in Woodlawn
4.9 out of 5 average rating, 196 reviewsA Stones Throw from U Chicago South Campus!
Condo in Logan Square
4.98 out of 5 average rating, 237 reviewsUrban Luxury 1BR/2BA Logan Square Condo w/Garage
Condo in Gold Coast
4.88 out of 5 average rating, 139 reviewsMARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Other great vacation rentals in Downtown Chicago
Guest suite in Lincoln Square
4.95 out of 5 average rating, 244 reviewsGreat location, private entry and patio!
Guest suite in Lincoln Square
4.92 out of 5 average rating, 405 reviewsPrivate Lincoln Square Garden Apt
Guest suite in Chicago
4.93 out of 5 average rating, 176 reviewsBike the Lakefront from a Sleek Urban Retreat
Home in Pilsen Historic District
4.95 out of 5 average rating, 328 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
Guesthouse in Lincoln Square
4.88 out of 5 average rating, 231 reviewsPrivate Coach house near Lincoln Square!
Guesthouse in Andersonville
4.91 out of 5 average rating, 345 reviewsPrivate, Charming, Coach House Loft in Andersonville
Guest suite in Chicago
4.98 out of 5 average rating, 114 reviewsGorgeous Studio 15 Minutes From Ohare!
Loft in Chicago
4.91 out of 5 average rating, 315 reviewsPilsen Modernist, Creative, Lightfilled Loft
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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