Vacation rentals in Downtown Chicago

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Popular amenities for Downtown Chicago vacation rentals

Other great vacation rentals in Downtown Chicago

Superhost
Home in Chicago
4.94 out of 5 average rating, 35 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

JessieRating, 5 stars4 weeks ago
Very nice, homey place. We felt right at home! Nice, quiet neighborhood.
Guest favorite
Home in Elmhurst
4.85 out of 5 average rating, 20 reviews

Enamored in Elmhurst

AshleyRating, 5 stars3 weeks ago
Mark was a great host. He went above and beyond! Made sure our stay was great the whole time we were there! Very responsive and accommodating! Definitely a great stay! Will be saving for future stays!
Guest favorite
Apartment in Chicago
4.85 out of 5 average rating, 127 reviews

Condo with private terrace, free WIFI and parking

OlegRating, 5 stars3 weeks ago
We have traveled to Chicago with a party of 5 - 3 adults and 2 kids in February 2025. We stayed for 3 nights and really liked Mark's place. It is really bigger than it shows on the pictures, so it really accomodates 6-8 people easily. Host was responsive and provided helpful and timely instructions. Would stay again.
Top guest favorite
Apartment in Chicago
4.95 out of 5 average rating, 41 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars1 month ago
Wonderful stay as always, thank you so much!
Superhost
Apartment in Chicago
4.74 out of 5 average rating, 19 reviews

City Gem: Stylish 3BR for Urban Explorers

BIVIANARating, 5 stars3 weeks ago
Everything was great! Thank you so much for everything!
Superhost
Condo in Chicago
4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars2 months ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.
Superhost
Home in Cicero
4.79 out of 5 average rating, 173 reviews

Spacious whole apt near shopping and city

ChristopherRating, 5 stars1 month ago
The BNB was in a convenient spot and Daniel was very communicative and helpful. I enjoyed my stay!
Top guest favorite
Home in Lombard
5 out of 5 average rating, 22 reviews

Spacious Home in Chicago Suburbs

ClydeRating, 5 stars3 weeks ago
The space was well decorated, spacious and perfect for our family. I really appreciated the fact that the house was nice and warm once we arrived considering the Chicago winter. Our family was able to be comfortable and enjoy our stay with no major issues.

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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