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
Other great vacation rentals in Downtown Chicago
Apartment in Chicago
4.89 out of 5 average rating, 140 reviewsCharming Gold Coast One-Bedroom Near Downtown!
Apr 10 – 17
Apartment in Little Italy
4.98 out of 5 average rating, 199 reviewsSpacious 2BR on Quiet St - Free Park/Late Checkout
Jan 20 – 27
Apartment in Cicero
4.98 out of 5 average rating, 202 reviewsCOZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy
Feb 25 – Mar 4
Apartment in West Town
4.89 out of 5 average rating, 473 reviewsiKlektik House Chicago / Robin
Oct 20 – 27
Apartment in East Rogers Park
4.89 out of 5 average rating, 105 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Oct 24 – 31
Apartment in Chicago
4.84 out of 5 average rating, 175 reviewsThe Cottage
Sep 26 – Oct 3
Apartment in Lincoln Square
4.94 out of 5 average rating, 191 reviewsSpacious, light-drenched studio-private entrance!
Jul 14 – 21
Apartment in Chicago
4.99 out of 5 average rating, 194 reviewsExplore Lincoln Park from a Polished Apartment
Feb 13 – 20
Downtown Chicago condo rentals
Condo in West Town
4.87 out of 5 average rating, 107 reviewsSpacious Duplex in Great Location
Oct 21 – 28
Condo in Lincoln Park
4.95 out of 5 average rating, 441 reviewsUnique Lincoln Park Duplex Apt
Sep 26 – Oct 3
Condo in Little Italy
4.96 out of 5 average rating, 120 reviewsPrivate hot tub - King bed suite - Free parking
Jun 14 – 21
Condo in Lake View
4.99 out of 5 average rating, 564 reviewsUrban Comfort in the Heart of Chicago
Jul 24 – 31
Condo in Lincoln Park
4.91 out of 5 average rating, 247 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
Dec 27 – Jan 3
Condo in Gold Coast
4.9 out of 5 average rating, 168 reviews2BD/2BA MAG MILE MASTERPIECE (+Rooftop)
Jul 9 – 16
Condo in West Town
4.95 out of 5 average rating, 131 reviewsGrand Avenue Apt 2/west Loop & Newly Renovated!
Condo in East Rogers Park
4.93 out of 5 average rating, 187 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Mar 2 – 9
Other great vacation rentals in Downtown Chicago
Loft in Lake View
4.96 out of 5 average rating, 420 reviewsLakeview Loft-Vintage Chicago, Modern Amenities
Mar 22 – 29
Guest suite in Chicago
4.92 out of 5 average rating, 115 reviewsEntirely Private Suite - Urban Oasis - Pilsen/UIC
Jul 6 – 13
Apartment in Logan Square
4.92 out of 5 average rating, 492 reviews2BR Bursting w/ Character in Hip Logan Square!
Apr 8 – 15
Apartment in Lincoln Square
4.81 out of 5 average rating, 124 reviewsTranquil & Airy 1BR Apt in Lincoln Square
May 7 – 14
Guest suite in Chicago
4.93 out of 5 average rating, 172 reviewsBike the Lakefront from a Sleek Urban Retreat
Oct 21 – 28
Guest suite in Irving Park
4.99 out of 5 average rating, 137 reviewsBnB on Grace Street - Modern 2-Bedroom Guest Suite
Oct 20 – 27
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 202 reviewsSpectacular Pilsen Studio for 2!
Dec 8 – 15
Guest suite in Lincoln Square
4.91 out of 5 average rating, 420 reviewsCozy, Quiet, Garden Getaway!
Oct 3 – 10
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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