Vacation rentals in Chicago
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Top-rated vacation rentals in Chicago
Guests agree: these stays are highly rated for location, cleanliness, and more.
Explore 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.
Secret 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.
Private Lincoln Square one bed+bath studio apt.
Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336
Sun 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!
Luxury Loft Collection 01 - Terrace - River North
BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious building in bustling River North-the city's center of main nightlife and restaurants. This ultra high-end apartment features a private elevator, private terrace, free secured parking, 24 hour doorman, 3 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!
Kasa | Walk to Lincoln Park Zoo | Chicago
When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.
Modern vintage chic steps from Wrigley: park free
Vintage touches and modern updates in the heart of Wrigleyville! Includes off street parking. Close enough to see Wrigley Field from the building, yet the block is charming and quiet. Close to the lake and Boystown. Charming vintage DNA meets modern amenities. Large deck. You will love the exposed brick and original millwork while enjoying huge new windows, an open floor plan, chef's kitchen, stylish decor, and spa like bathroom. Chicago Shared Housing Registration: R22000093584
Lovely top floor 2BR/2BA, steps from everything!
BEST LOCATION IN LOGAN SQUARE/AVONDALE! Brand new stylish TOP floor 2 bed/2 bath located in the heart of the highly desirable Avondale neighborhood. This luxurious space is situated 15 minutes drive to Wrigley Field, 7 minutes walk from the CTA Belmont Blue Line, only minutes away from O'Hare airport, downtown Chicago and The Loop. Conveniently close to expressway. Steps from award winning restaurants, popular bars, great coffee shops, clubs, galleries and exclusive shops.
Penthouse Near Wrigley Field
This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.
Chic 2BR Gem with Fireplace
Discover urban luxury in our 2BR, 2BA Gold Coast haven. This stylish apartment boasts a warm fireplace, sleek granite countertops, and a cozy layout. Immerse yourself in city living at its finest, right in the heart of Chicago's prestigious Gold Coast neighborhood. Perfect for both business and leisure travelers, our space combines modern comfort with the vibrant energy of one of the city's most coveted neighborhoods.
"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux
Urban-Luxe experience at the Bliss of Evanston Condo. Elegant finishes and a sweeping Sky Terrace view of downtown Evanston. Resort-like amenities with fitness center, outdoor pool, free parking in indoor GAR, biz ctr, and much more. 2 bedrooms, 2 full baths, 2 roll-out beds welcome you to a comfortable stay near Northwestern University, Loyola, and Kellogg and minutes from Chicago Downtown.
Relax & Walk to Wrigley Field from this Comfy Home
Stay at this two-bedroom, two-bathroom garden apartment on a beautiful tree-lined street in Chicago's North Center neighborhood. Wrigley Field is just over a mile away and Lake Michigan is two miles east. The brick building is also walking distance to restaurants, bars, a brewery, Trader Joe's grocery, and public transportation.
Popular amenities for Chicago vacation rentals
What Airbnb hosts recommend seeing in Chicago
Find unforgettable activities and unique points of interest near you. Our hosts share their favorite things to do and must-visit places to see in Chicago.
Millennium Park
Urban oasis featuring iconic public art, lush gardens, and free cultural events
Summarized by AI
At Millennium Park you can photograph your reflection at Cloud Gate (“the Bean”), cool off in Crown Fountain, wander the Lurie Garden, and explore public art, Wrigley Square, and the pine forest along the walking paths. Catch free concerts, movies, festivals, and classical performances at the Frank Gehry–designed Jay Pritzker Pavilion, or join free outdoor workouts like tai chi, yoga, Pilates, and Zumba on summer Saturdays. In winter, skate the ribbon; in warmer months, enjoy rock climbing and kid-friendly play areas, with Maggie Daley Park just across the pedestrian bridge.
Wrigley Field
Historic baseball stadium featuring ivy-covered walls, a hand-turned scoreboard, and lively surrounding bars
Summarized by AI
At Wrigley Field you can catch a Chicago Cubs game, eat a classic Chicago hot dog or a memorable sausage from Hot Doug’s, and take in the ivy-covered brick walls, iconic red marquee, and manually operated scoreboard. Join an in-season or behind-the-scenes tour to visit the press box, locker rooms, batting cages, dugouts, and even up by the scoreboard. In summer, come for occasional concerts, and in colder months check out the Christmas Market and Winter Wonderland. Afterward, linger in Wrigleyville’s bars and Gallagher Way to keep the game-day energy going.
United Center
Premier sports and entertainment venue home to the Bulls, Blackhawks, and major concerts
Summarized by AI
Step into Chicago’s largest indoor arena to watch the Chicago Bulls and Chicago Blackhawks play on their home court and ice, or catch major concerts, Disney on Ice, the circus, and other large-scale shows. Inside, look up at the 58 championship banners and visit the 12-foot bronze statue of Michael Castro for a photo with #23. The United Center also hosts big events like political conventions, college tournaments, and world-famous tours. After your event, you can grab a Cheezborger at nearby Billy Goat Tavern.
Navy Pier
Vibrant waterfront destination with attractions, dining, and stunning views of Lake Michigan
Summarized by AI
At Navy Pier you can ride the 150-foot Centennial Ferris wheel, historic carousel, and other carnival rides, explore the Chicago Children’s Museum and indoor glass maze, see a show at Chicago Shakespeare Theater, or catch a film at the IMAX theater. Stroll through the Crystal Gardens indoor botanical garden, browse shops, and try multiple Chicago restaurants, bars, dessert spots, and the large rooftop bar at the end of the pier. In summer, enjoy lake cruises, sightseeing and dinner boats, live bands, and fireworks every Wednesday and Saturday night. Seasonal events like Winter WonderFest add indoor rides, giant slides, ice skating, and holiday décor for families.
Soldier Field
Historic stadium hosting Chicago Bears games, concerts, and major events
Summarized by AI
Catch a Chicago Bears NFL game or a Chicago Fire soccer match at Soldier Field, where the energy from passionate fans, team colors, and loud chants fills this open-air stadium. Enjoy major concerts and festivals here too—everyone from Beyoncé to the Rolling Stones has performed in this iconic venue. Built in 1924 and later modernized, it combines historic colonnades with views of Lake Michigan and the skyline. Even on non-game days, it’s a landmark for soaking up Chicago sports history and taking memorable photos.
Humboldt (Alexander Von) Park
Expansive park with lagoons, sports fields, a boathouse, and cultural attractions
Summarized by AI
At Humboldt Park you can walk or run miles of trails, relax on the grass, or set up a picnic by the lagoons, inland beach, or waterfall. Rent giant swan paddle boats at the historic boathouse, play tennis, soccer, or baseball, let kids loose on multiple playgrounds, or watch birds and other wildlife in the bird sanctuary and prairie-style gardens. In summer, look for Puerto Rican food trucks around the park, then head to nearby Division Street for jibaritos and other Puerto Rican dishes.
Private Chicago vacation rentals
A bit of the North Woods on Chicago's North Side!
Archways at the Lincoln Park Zoo 2bed/2ba
Former Artist Studio
A guest suite centrally located, but so quiet
Your perfect place looks like?
Sunny 1 bedroom apartment 1 block from restaurants
Spectacular Penthouse Corner 2BR in Streeterville
Eddy Street Upstairs Apartment
Pet-friendly vacation rentals in Chicago
Wicker Park Walk-Up Condo
Sounds Of The City
RockStar Pad W3A BoysTown/Wrigley Field/Parking lot
The Chicago River House – GIANT wall projector!
Stylish Studio in Historic Logan Square
Victorian House in Heart of Rogers Park
Modern Luxury In Old Town - Sleeps 4
Charming 3-BED in Lincoln Park/ Old Town & Parking
Vacation rentals with jacuzzis in Chicago
Lux Urban 3BR/3BA Duplex + Parking!
Modern Getaway w/ Hot Tub, Lrg Yard, Parking
Explore Fulton Market + Retreat in Modern Comfort
Tea Studio in Wicker Park Spring Factory
Downtown Chicago - Spa Bath, Patio, 3 blocks to L
The Spa of Downtown Whiting
Belmont Pleasures - hot tub / arcade gaming room
Family 7BD Home with Game Rm, Hot Tub, and Sauna
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ404 | ﺩ.ﺇ411 | ﺩ.ﺇ459 | ﺩ.ﺇ474 | ﺩ.ﺇ544 | ﺩ.ﺇ569 | ﺩ.ﺇ573 | ﺩ.ﺇ588 | ﺩ.ﺇ529 | ﺩ.ﺇ529 | ﺩ.ﺇ474 | ﺩ.ﺇ452 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Frequently Asked Questions
What are the best places to stay in Chicago?
Explore neighborhoods like the Loop for architecture and theater, River North for art galleries and dining, or Wicker Park for music and locally owned shops. Lincoln Park is often suggested for access to parks and museums. Each area has a distinctive vibe shaped by arts, food, and community events.
What are the best things to do in Chicago with kids?
Families often explore Shedd Aquarium, the interactive exhibits at the Museum of Science and Industry, and the playful areas at Millennium Park. Maggie Daley Park has climbing walls and play gardens around the park. Chicago’s lakefront paths also invite bike rides and strolls.
What are some of the best things to do in Chicago?
Explore public art at Millennium Park, admire city views from Willis Tower’s Skydeck, or step inside the Art Institute of Chicago. Neighborhoods like Pilsen and Hyde Park have murals and museums with local flavor. The city’s music scene and riverwalk are also popular.
How is the weather in Chicago?
Chicago has cold, often snowy winters with temperatures near 19–33°F (-7–0°C) in January and warm, humid summers around 68–85°F (20–29°C) in July. Spring and fall bring milder, changeable weather. Layers and a windproof jacket can help with breezy days.
What are the best places to visit in Chicago?
Explore the Art Institute of Chicago for world-famous collections, stroll Grant Park’s gardens, or discover Navy Pier’s rides and views. Lincoln Park Zoo and the Field Museum are frequently suggested for learning and family activities. Riverwalk paths connect public art and city life.
What are some hiking trails in Chicago?
The city has paved trails like the Lakefront Trail, winding along the waterfront with parks and skyline views. North Park Village Nature Center has natural paths in a woodland setting. Jackson Park features walking trails amid gardens and lagoons.
What are some family activities we can do in Chicago?
Families can enjoy Cloud Gate in Millennium Park, visit the Shedd Aquarium, or experience hands-on exhibits at the Chicago Children's Museum. Maggie Daley Park has playgrounds, gardens, and seasonal skating. The Lincoln Park Zoo is also popular for its no-fee entry.
What are some of the best day trip ideas from Chicago?
Explore historic towns known for architecture and artists, unwind at nearby lakefront beaches, or visit protected forest preserves with hiking and biking. In warmer months, local farms sometimes have markets and seasonal activities. Regional parks are frequently suggested for nature outings.
Are there any pet friendly accommodations available in Chicago?
Many vacation rentals welcome pets in neighborhoods like Lakeview, Logan Square, and West Loop. The city has dog-friendly parks and outdoor patios where pets can relax with their people. Always confirm pet policies with your host before booking.
What are some local tips for visiting Chicago?
Layer clothing for changing lakefront weather and use public transit to explore neighborhoods beyond downtown. Try local food favorites at corner shops and explore smaller galleries or shops around Pilsen or Andersonville. Many beaches and parks are free and open to all.
What is Chicago known for?
Chicago is known for its skyline, jazz and blues music roots, and locally rooted culinary traditions like deep-dish pizza and Chicago-style hot dogs. The city also has a strong history of public art and diverse neighborhoods. Architecture tours and live theater are frequently suggested.
What are the best hidden gems to explore in Chicago?
Explore murals and independent coffee shops in Pilsen, or the Victorian houses and gardens in the Prairie District. The Alfred Caldwell Lily Pool and the Chicago Cultural Center’s Tiffany dome are often described as peaceful escapes. Quirky museums and bookstores also dot many neighborhoods.
What are the best foods to try in Chicago?
Chicago-style deep-dish pizza, Italian beef sandwiches, and Chicago-style hot dogs are frequently suggested signature foods. Try popcorn mixes, fried chicken, or savory pierogi in neighborhoods known for their food scenes. Bakeries often serve cheesecake and traditional sweets as well.
What should I bring for a trip to Chicago?
Pack weather-appropriate layers, a windproof jacket, and comfortable shoes for walking. Consider an umbrella or raincoat for spring or fall visits, and sun protection in summer. If you plan to explore the lakefront, bring a refillable water bottle and sunglasses.
What is the nightlife in Chicago like?
Chicago has live music venues, jazz lounges, and comedy clubs in neighborhoods like River North, Wicker Park, and Uptown. Many areas have late-night dining and lively bars. Nightlife here often centers on a mix of music, food, and local performers.
What are the most popular events or festivals in Chicago?
Chicago hosts music festivals in summer, large food celebrations, and the citywide Chicago Air and Water Show. Lollapalooza and the Chicago Blues Festival draw crowds in warmer months, while winter brings holiday light displays and parades. Outdoor neighborhood street fairs run throughout the year.
Are there family friendly vacation rentals in Chicago?
Many vacation rentals in Chicago are family friendly, especially in neighborhoods like Lincoln Park, Lakeview, and Bucktown. These areas are known for access to parks, playgrounds, and dining suited for all ages. Hosts often include information about local family activities.
When is the best time to visit Chicago?
Late spring to early fall is often recommended for milder weather, outdoor events, and green city parks. Winter brings festive lights and ice skating but requires warm clothing. Each season has its own rhythm shaped by events and changing lakefront scenery.
All about Chicago
Settled along the banks of Lake Michigan, the Windy City of Chicago offers world-class dining, exciting architecture, a top performing arts scene, and plenty of excellent museums. With more than 200 neighborhoods calling this city home, there’s a unique aura found in each.
You’ll find historic mansions and upscale shopping in Gold Coast, Gothic-style university buildings in Hyde Park, cool cocktail bars and quirky shops in hip Logan Square, and incredible comedy clubs in Old Town. Enjoy time outside lounging on the city beaches, catch a baseball game at Wrigley Field, shop along the Magnificent Mile, or sample the celebrated dining scene in this dynamic city, the third-largest metropolis in the United States.
What are the top things to do in Chicago?
The Art Institute of Chicago
The Art Institute is one of the best museums in the United States with more than 300,000 permanent artworks and many traveling exhibits. Take shelter from the city’s infamous wind and check out world-famous paintings from French Impressionists and modern American masterpieces. Cafes and restaurants are on-site for coffee breaks and leisurely lunches, and the museum also hosts regular lectures and events.
Willis Tower
The tallest building in the world for almost 25 years, the Willis Tower is a 110-story skyscraper that’s now the second-tallest building in the U.S. For a view that can reach Wisconsin and Michigan on a clear day, visit The Willis Tower observation deck. It’s located on the 103rd floor of the building, and you can even step inside glass observation boxes that extend four feet over the street below.
Millennium Park
Located across from the Art Institute, this city park is one of the most recognizable areas in Chicago thanks to the iconic Cloud Gate sculpture, lovingly known as “The Bean.” Rotating sculpture exhibitions and the naturalistic Lurie Garden make for lovely visits in spring and fall. During the summer months, the park comes alive with outdoor concerts, film screenings, dance performances, and even public yoga classes.
Quick stats about vacation rentals in Chicago
Total vacation rentals
Explore 11,110 vacation rentals in Chicago
Verified guest reviews
Over 591,960 verified reviews to help you choose
Family-friendly vacation rentals
5,510 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 3,820 rentals that welcome pets
Vacation rentals with a pool
1,270 properties feature pools
Rentals with dedicated workspaces
7,040 properties have a dedicated workspace
Wi-Fi availability
10,940 of Chicago vacation rentals include wi-fi access
Popular amenities for guests
Guests love Self check-in, Monthly stays, and Lake access across Chicago rentals
4.7 Average rating
Chicago stays receive an average rating of 4.7 out of 5 from guests
Nearby attractions
Chicago's top spots, include Millennium Park, Wrigley Field, and Lincoln Park
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- 875 North Michigan Avenue
- Soldier Field
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Brookfield Zoo
- Illinois Beach State Park
- Willis Tower
- University of Chicago
- Washington Park Zoo
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