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Downtown Chicago vacation rentals
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Top-rated vacation rentals in Downtown Chicago
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Downtown Chicago condo rentals
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Condo in Chicago
4.87 out of 5 average rating, 131 reviews3D Tour! Designer Condo near Logan Square
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Condo in Chicago
4.96 out of 5 average rating, 133 reviewsPrivate hot tub - King bed suite - Free parking
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Condo in Chicago
4.88 out of 5 average rating, 112 reviewsSpacious Duplex in Great Location
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Condo in Chicago
4.87 out of 5 average rating, 126 reviewsQuiet, Modern, Convenient 2 bedroom condo
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Condo in Chicago
4.96 out of 5 average rating, 449 reviewsUnique Lincoln Park Duplex Apt
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Condo in Chicago
4.99 out of 5 average rating, 578 reviewsUrban Comfort in the Heart of Chicago
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Condo in Chicago
4.92 out of 5 average rating, 117 reviewsStunning, Spacious, & Sun-Soaked 1br Uptown Condo
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Condo in Chicago
4.97 out of 5 average rating, 109 reviewsStylish 3BR + Free Parking 10-15mins from Downtown
Downtown Chicago apartment rentals
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Rental unit in Chicago
4.98 out of 5 average rating, 111 reviewsHumboldt Park Loft
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Rental unit in Chicago
4.98 out of 5 average rating, 203 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
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Rental unit in Cicero
4.98 out of 5 average rating, 217 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
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Rental unit in Chicago
4.84 out of 5 average rating, 178 reviewsThe Cottage
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Rental unit in Chicago
4.98 out of 5 average rating, 308 reviewsRedesigned Lower Level Studio in Historic Building
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Rental unit in Chicago
4.88 out of 5 average rating, 252 reviewsModern
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Rental unit in Chicago
4.96 out of 5 average rating, 105 reviewsCute, Clean, Cozy Apartment in Pilsen
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Rental unit in Chicago
4.78 out of 5 average rating, 140 reviewsRoomy Getaway in Vibrant Center of Lincoln Park
Other great vacation rentals in Downtown Chicago
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Loft in Chicago
4.96 out of 5 average rating, 427 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
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Home in Chicago
4.95 out of 5 average rating, 332 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
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Guest suite in Chicago
4.96 out of 5 average rating, 313 reviewsAugusta's Garden | Noble Square | Wicker Park
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Guest suite in Chicago
4.95 out of 5 average rating, 182 reviews1 mile from Wrigley Field
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Rental unit in Chicago
4.85 out of 5 average rating, 244 reviewsTeeny Tiny Bohemian Lodge - Clean & Affordable
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Rental unit in Chicago
4.93 out of 5 average rating, 196 reviewsSpacious, light-drenched studio-private entrance!
Rental unit in Chicago
4.92 out of 5 average rating, 337 reviewsBright, Modern Apartment in a Vintage Greystone
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Rental unit in Chicago
4.82 out of 5 average rating, 445 reviewsLovely Andersonville Apt with Ideal Location
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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