
Downtown Chicago vacation rentals
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Top-rated vacation rentals in Downtown Chicago
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Apartment in Chicago
4.82 out of 5 average rating, 325 reviewsSophisticated, Historic & Comfy Flat near Wrigley!
Down comforters, nice towels and linens + stylish design and comfort You will have access to the entire space - 4 bedrooms, 2 bathrooms, living room, dining room, kitchen, back deck, and back yard. Send me a text or call. This home is in the heart of it all, just a 10-minute drive to the lake, beach, and Wrigley Field. A strip mall is close by with different food outlets. Uptown's Green Mill Jazz club, Riviera Theatre, and Aragon Ballroom are a short bus ride away. The Montrose Brown Line stop is a 7 minute walk directly west. The #22 bus is a 2 minute walk away and takes you to Wrigleyville (south 10 mins) and Andersonville (North 10 mins) The #78 bus stops right outside and can take you Montrose Beach (east 10 mins) or to the Blue Line airport transfer (west about 25 minutes) Free Street parking on Montrose or Ashland is usually available. Deluxe California King Blowup Mattress available for living room. Very comfortable.

Apartment in Chicago
5 out of 5 average rating, 243 reviewsExplore Lincoln Park from a Polished Apartment
This apartment is a large studio in the heart of Lincoln Park! New construction and all furnishings & appliances are brand new. It is perfect for a couple...but can also sleep 3-4 for a girls trip or a family with small children. You enter with your personal keypad code which we give you a few days prior to your stay. And we are always available by text or email should you have any questions about the apartment. Set in Lincoln Park, this apartment is steps away from shopping along Armitage and Halsted Avenue. There’s grocery stores, restaurants, and cafes nearby, plus red and brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment and we offer free residential parking stickers in the apartment on the desk. We also offer a clean garage space (with free EV hook up, should you need it) for $20/night.

Guest suite in Chicago
4.96 out of 5 average rating, 331 reviewsSecret Garden @ The Noble Farmhouse | Wicker Park
While our place truly is a tucked away secret sanctuary, we are also in a sweet spot of ULTRA CONVENIENCE. Wicker Park/Noble Square/West Town has many great bars & restaurants & is an amazing location for exploring the city. WALK to the action on Division St. or Chicago Ave, Chicago's upcoming gallery district. A 1/2 block to the 56 bus takes you to the Loop in 10 min, or to the heart of Wicker Park in 5. A 10 min walk to the BLUE LINE serving O'Hare & Downtown. And Divvy bikes 1/2 block away.

Apartment in Chicago
4.94 out of 5 average rating, 160 reviewsSun drenched 2 bedroom 1 bath with Kitchen & W/D
Welcome to beautiful Roscoe Village! Come relax and enjoy a gorgeous loft-like condo that has a huge sun-drenched living room and opens up right to the kitchen. Enjoy cooking on your own in the spacious kitchen and rest easily at night in a spacious king bed in the main bedroom. We love and welcome pets - so no need to leave your fur baby at home. Uber to Wicker Park and Logan Square. You’ll have your own private entrance with a lock box to get into the condo. We look forward to hosting you!

Home in Chicago
4.88 out of 5 average rating, 167 reviewsLake View | Wrigley Designer House w/Patio
Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

Home in Chicago
4.91 out of 5 average rating, 174 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Apartment in Chicago
4.83 out of 5 average rating, 109 reviewsChic Penthouse In Perfect Wrigleyville Location
Bright and open top floor apartment within easy walking distance to many of the best sites in Chicago: Wrigley Field, Lake Michigan, Lincoln Park, top notch neighborhood restaurants, pubs, and entertainment, and many more! With so much to do in the area and easy access to public transit you're sure to have jam-packed days of exploring and enjoying the city. After a long day, come back to this peaceful apartment to relax, recharge, and prepare to do it all again tomorrow. Book today!

Apartment in Chicago
4.91 out of 5 average rating, 11 reviews2-level PH w/ 2 Luxe Suites Combined; Spa Access
The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: -Uber-fast Wifi streaming, -Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches for living - Designed for an aristocratic feel - The touristy 606 Trail access 100ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Home in Chicago
5 out of 5 average rating, 9 reviewsAlluring Avondale Abode
Welcome to Alluring Avondale Abode, the perfect vacation rental for your next family trip or group getaway. A pet-friendly paradise, centrally located for easy travel to all the top attractions. A spacious kitchen, beautiful backyard deck, and patio create a wonderful backdrop for entertaining and relaxing. Find an array of fun games to keep all ages occupied. Book now and experience the laid-back vibe and unbeatable amenities that will make your vacation truly unforgettable.

Apartment in Oak Park
4.75 out of 5 average rating, 145 reviews1BR Apartment - Walk to Shops - Downtown OAK PARK
Your family will be close to everything when you stay at this centrally-located place. - 4 min drive to the train - 2 min drive to grocery stores & shopping - 20 min drive to Downtown Chicago Enjoy the historic neighborhood and see Frank Lloyd architecture nearby. ➢ Everything is sanitized/washed/cleaned after every guest ➢ Fast, Dedicated Wifi ➢ 2 Smart TVs (Living Room, Bedroom) ➢ Fully equipped + stocked kitchen / bathroom ➢ Pack 'n Play

Guesthouse in Oak Park
4.96 out of 5 average rating, 102 reviewsO'Malley Oasis!
Your home away from home at this centrally-located coachhouse apartment.Queen sized bed, fully equipped eat-in kitchen, relaxing living area with recliner, leather couch and big screen tv. Walk to downtown or explore Chicago via public transportation just a few blocks away. Adorable porch and your own entry. Parking spot included!

Apartment in Chicago
4.96 out of 5 average rating, 278 reviewsSpacious 1BR apartment in a central location
Private 1BR in Avondale neighborhood of Chicago. Right off the Expressway, it's 20 mins from O'Hare, 20 mins from Downtown (both by Blue Line) 20 mins from Wrigley Field (bus). Comfortable and spacious attic apartment in a residential area. Lots of street parking.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Downtown Chicago vacation rentals
Pet-friendly vacation rentals in Downtown Chicago

Home in Chicago
4.94 out of 5 average rating, 122 reviewsSpacious Full Home Near the Heart of Wrigleyville

Apartment in Evanston
4.82 out of 5 average rating, 170 reviewsMDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Townhouse in Chicago
4.85 out of 5 average rating, 164 reviewsDowntown Elegance ✨ Private Yard Parking

Apartment in Forest Park
4.86 out of 5 average rating, 237 reviewsHome in Forest Park downstairs.

Condo in Chicago
4.91 out of 5 average rating, 329 reviewsSusie's Space. 2BR easy parking & pet friendly

Apartment in Oak Park
4.82 out of 5 average rating, 179 reviewsReno btrm; Big family escape, W/parking, love pets

Apartment in Palos Hills
4.94 out of 5 average rating, 168 reviewsAunt Linda's Apartment with a View in Palos

Townhouse in Chicago
4.84 out of 5 average rating, 112 reviewsWrigleyville townhome two blocks from ballpark
Vacation rentals with jacuzzis in Downtown Chicago

Condo in Chicago
4.8 out of 5 average rating, 161 reviewsModern Wrigley Oasis with Parking!

Home in Chicago
4.85 out of 5 average rating, 311 reviewsLux Urban 3BR/3BA Duplex + Parking!

Home in Chicago
4.96 out of 5 average rating, 113 reviewsModern Lux Getaway w/ Hot Tub, Lrg Yard, Parking

Loft in Chicago
4.96 out of 5 average rating, 244 reviewsTea Studio in Wicker Park Spring Factory

Condo in Chicago
4.93 out of 5 average rating, 107 reviewsThe Fox Den

Condo in Chicago
4.96 out of 5 average rating, 121 reviewsDowntown Chicago - Spa Bath, Patio, 3 blocks to L

Home in Whiting
4.84 out of 5 average rating, 146 reviewsThe Spa of Downtown Whiting

Condo in Chicago
4.96 out of 5 average rating, 179 reviewsPrivate hot tub - King bed suite - Free parking
Downtown Chicago apartment rentals

Apartment in Chicago
4.98 out of 5 average rating, 103 reviewsLovely 2bedroom 1bath Apt and outdoor seating.

Apartment in Summit
4.89 out of 5 average rating, 108 reviews2BR Apartment Near Chicago

Apartment in Chicago
4.95 out of 5 average rating, 111 reviewsElegant Depaul Apt on Jonquil Park

Apartment in Evanston
4.84 out of 5 average rating, 245 reviewsAdorable 1BR apartment near Northwestern

Apartment in Chicago
4.92 out of 5 average rating, 154 reviewsExecutive Apartment on Lake Michigan with parking

Apartment in Chicago
4.99 out of 5 average rating, 200 reviewsChicago Airbnb Newly Remodeled 2-Unit Apartment!

Apartment in Chicago
4.97 out of 5 average rating, 139 reviewsInviting 2 Bedroom Apartment in Roscoe Village

Apartment in Chicago
4.82 out of 5 average rating, 254 reviewsBERNARD CHATEAU - LOGAN SQUARE
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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