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, 282 reviewsRoscoe Village One Bed Lux Apartment Near Wrigley
Rental unit in Chicago
4.93 out of 5 average rating, 147 reviewsSun drenched 2 bedroom 1 bath with Kitchen & W/D
Rental unit in Chicago
4.95 out of 5 average rating, 286 reviewsTurquoise Wonder - Clean, Cozy & Stylish Apt
Rental unit in Chicago
4.86 out of 5 average rating, 518 reviewsLogan Square Studio
Rental unit in Chicago
4.93 out of 5 average rating, 416 reviewsRavenswood Guest House Annex
Rental unit in Chicago
4.9 out of 5 average rating, 171 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Rental unit in Chicago
4.98 out of 5 average rating, 341 reviewsRedesigned Lower Level Studio in Historic Building
Rental unit in Chicago
4.98 out of 5 average rating, 121 reviewsElegant Suite in Gold Coast
Downtown Chicago condo rentals
Condo in Chicago
4.89 out of 5 average rating, 150 reviewsMARVELOUS MAG MILE 2BD/2BA (+Rooftop)
Condo in Chicago
4.9 out of 5 average rating, 102 reviewsUnique 2BR/2BA FREE Parking/WI-FI Minutes From DT
Condo in Chicago
4.96 out of 5 average rating, 111 reviewsDowntown Chicago - Spa Bath, Patio, 3 blocks to L
Condo in Chicago
4.86 out of 5 average rating, 167 reviews3D Tour! Designer Condo near Logan Square
Condo in Chicago
4.97 out of 5 average rating, 157 reviewsSunny Tri Level
Condo in Chicago
4.91 out of 5 average rating, 327 reviewsSusie's Space. 2BR easy parking & pet friendly
Condo in Chicago
4.78 out of 5 average rating, 167 reviewsCabin 301 at 747 Lofts
Condo in Chicago
4.94 out of 5 average rating, 133 reviewsCHIC DOWNTOWN PENTHOUSE w/ private roof +parking
Other great vacation rentals in Downtown Chicago
Guest suite in Chicago
4.88 out of 5 average rating, 111 reviewsCozy one-bedroom suite in the heart of West Loop
Guest suite in Chicago
4.93 out of 5 average rating, 95 reviewsLogan Square Garden Suite
Rental unit in Chicago
4.84 out of 5 average rating, 115 reviewsPilsen Blue Door
Guesthouse in Chicago
4.99 out of 5 average rating, 828 reviewsPolk Street Coach House Apartment, Little Italy/Medical Dist
Rental unit in Chicago
4.87 out of 5 average rating, 60 reviewsMAG MILE Designer Flat - Steps to the Lake!
Home in Berwyn
4.99 out of 5 average rating, 116 reviewsRetro Modern Bungalow— fire pit + free parking
Rental unit in Chicago
4.86 out of 5 average rating, 296 reviewsCharming loft style suite
Rental unit in Chicago
4.92 out of 5 average rating, 198 reviewsCharming Apt. near Wrigley/Cubs, Ravenswood/Uptown
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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