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 Lincoln Park
4.98 out of 5 average rating, 296 reviewsRedesigned Lower Level Studio in Historic Building
Oct 3 – 10
Apartment in Chicago
4.84 out of 5 average rating, 174 reviewsThe Cottage
Sep 11 – 18
Apartment in Chicago
4.99 out of 5 average rating, 192 reviewsExplore Lincoln Park from a Polished Apartment
Feb 6 – 13
Apartment in Chicago
4.98 out of 5 average rating, 127 reviewsModern Apt with style & comfort in Pilsen Chicago
Jul 8 – 15
Apartment in Chicago
4.99 out of 5 average rating, 171 reviewsComfy River West Apt with Free Parking
Apr 20 – 27
Apartment in Chicago
4.95 out of 5 average rating, 103 reviewsComfortable, modern apartment 20 Min from Downtown
Nov 4 – 11
Apartment in East Rogers Park
4.89 out of 5 average rating, 105 reviewsLAKESIDE PIED `A TERRE STEPS TO BEACH
Feb 17 – 24
Apartment in Logan Square
4.96 out of 5 average rating, 255 reviewsLogan Square 2nd Floor Chicago Victorian
Mar 22 – 29
Downtown Chicago home rentals
Home in Chicago
4.95 out of 5 average rating, 117 reviewsCozy & Modern Chic Full House in Trendy Bridgeport
Nov 30 – Dec 7
Home in Chicago
4.96 out of 5 average rating, 313 reviewsGet Cozy at a Powder-Blue Residence in the Heart of Pilsen
Dec 28 – Jan 4
Home in Chicago
4.95 out of 5 average rating, 169 reviewsParadise on the Park
Oct 2 – 9
Home in Lake View
4.98 out of 5 average rating, 203 reviewsWrigleyville Southport Studio
Oct 18 – 25
Home in Berwyn
4.92 out of 5 average rating, 237 reviewsPrivate apartment with retro vibe
Sep 5 – 12
Home in Uptown
4.89 out of 5 average rating, 332 reviewsPrivate 3rd Floor Apartment
Dec 15 – 22
Home in Avondale
4.86 out of 5 average rating, 215 reviewsThe Avondale Guesthouse
Dec 22 – 29
Home in Chicago
4.96 out of 5 average rating, 199 reviewsDivision St Designer Home In Heart of Wicker Park
May 20 – 25
Downtown Chicago condo rentals
Condo in West Town
4.87 out of 5 average rating, 105 reviewsSpacious Duplex in Great Location
Aug 25 – Sep 1
Condo in Little Italy
4.96 out of 5 average rating, 117 reviewsPrivate hot tub - King bed suite - Free parking
Jun 17 – 24
Condo in Lincoln Park
4.95 out of 5 average rating, 436 reviewsUnique Lincoln Park Duplex Apt
Sep 28 – Oct 5
Condo in West Town
4.86 out of 5 average rating, 435 reviewsHumboldt Park Traveler's Lodge
May 21 – 28
Condo in Chicago
4.95 out of 5 average rating, 174 reviewsUpdated Designer Duplex In Fulton Market W/parking
Feb 21 – 28
Condo in North Center
4.91 out of 5 average rating, 118 reviewsSpacious & Modern Family Friendly North Center Apt
Jan 14 – 21
Condo in East Rogers Park
4.93 out of 5 average rating, 183 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
Dec 4 – 11
Condo in Chicago
4.91 out of 5 average rating, 244 reviewsOld Town Pied-à-Terre w/Pvt Terrace and Parking
Aug 2 – 9
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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