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.
Cool Quiet Coach House, Private Access + Patio
Retreat to the brick patio of this lovingly renovated home after a long day traversing the neighborhood. The interior is an expression of creativity, greyscale walls, rustic accents, and a varied selection of art and wall hangings tie in the decor. Split Level Floor plan. 1st floor = Living, Eat in Kitchen, bedroom 1 and bathroom. 2nd Floor = 2nd bedroom , bath and an additional sleeping area and desk area. Also features a gorgeous shared yard. The entire coach house is yours!! The coach house is set back behind a 2 unit building and the yard is shared between both. We are available via text or airbnb messaging and try to respond quickly. Please reach out anytime if you need anything at all. Extra supplies, neighborhood recommendations or tips in the neighborhood. The home is located on the border of Wicker Park and Bucktown which is Chicago's original hub of cool. It is a vibrant enclave of culture and commerce, explore vintage finds, record stores, and plenty of indie shopping in this trendy part of town The 24 hour Blue Line EL train is just a 5 minute walk. Door to Door it's only 25 minutes to Millennium park. (5 min walk to the blue line, 10 min ride on the train, 10 minute walk to the Park). The neighborhood is pedestrian and bike friendly , the 606 trail is just a few blocks away also.
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
CASA NEWPORT
Second floor, one bedroom apartment, with an additional queen pullout couch located in a beautiful historic district in Lakeview. Just steps away from Halsted street/Boystown/Wrigley field. Conveniently located to shopping, restaurants, subway (EL) and grocery stores. Close to lakefront, jogging path and bike path. Complementary street parking passes available. The apartment does NOT have airconditioning. It does have a window unit in the bedroom from April to September.
Lovely Garden Studio in Chicago
Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.
Belmont Pleasures - hot tub / arcade gaming room
Welcome home! If you’re looking for a unique experience to enjoy with your friends and family come have some fun in this beautiful luxury home, located in belmont-cragin neighborhood Chicago IL 60634 The spacious house includes 3 bedrooms, 4 full bunkbeds , 2 queen beds , 2 sofa queen beds , 2 & 1/2 bathrooms . Whether you’re looking to book for a birthday, bachelor/bachelorette gathering, or trip with family and friends, this place has something for everyone.
Division St Designer Home In Heart of Wicker Park
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined street, you’ll be only steps to the cafes, restaurants, bars, and shops that flank trendy Division Street; a short walk to the vibrant Chicago Ave and Milwaukee Ave restaurant & retail corridors. Just off the Division Blue Line “L” stop, we’re just a quick train ride to both the Downtown Loop (8 minutes) and O’Hare International Airport (35 minutes).
Quirky Quarters at Wrigley
I think you are just going to love my apartment. The space features wonderful large street level windows in the living room and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a ten minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. There is no parking available with the apartment.
Chic retreat near the best of Lakeview & Wrigley
Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!
Modern 3BR with Private Rooftop & Free Parking
A beautiful and modern 2450 sq feet apartment with a private rooftop deck, a rooftop firepit, an additional private patio and yard, brand new appliances, and bright spacious interior. Free private on-premise parking (1 garage spot and one driveway spot) in the heart of Chicago and a blocks walk to the L-transit system provides easy access to both downtown, the greater Chicago area, and both major airports.
Modern Izakaya Studio in Wicker Park
The Izakaya Studio is a sleek, design-forward space in the heart of Wicker Park, with a secret whisky room inside. Inspired by the intimate atmosphere of a Japanese izakaya: warm, curated, a little unexpected. The kind of place where you settle in, pour something good, and stop thinking about your plans for a while. Spacious for a studio, and comfortable enough for a longer stay in Chicago.
Vibrant & Chic Apt On Quiet St in Andersonville
Welcome to this thoughtfully remodeled 1925’s two-flat building located in the Second Coolest Neighborhood in the US. While this stylish space is the perfect relaxing stay, its location makes it easy for you to get around. *Free street parking You are only: 5 min walk to Clark St & Exceptional restaurants & bars 6 min drive to Lakefront & Lakeshore Drive... 17 min drive to Downtown Chicago...
Paradise on the Park
Located in Chicago’s hot West Town neighborhood. This is a one bedroom one bath unit in a quiet nook directly on Smith Park. Access to the park across the street with pickle ball courts, tennis courts, baseball field, and picnic areas. Situated close to Wicker Park and Bucktown. Plenty of FREE street parking directly across the street on the park side of the street.
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
Designer Garden Unit in Bridgeport
Sun drenched 2 bedroom 1 bath with Kitchen & W/D
Level Junior Two Bedroom Suite | Fulton Market
Cozy 2BD 2BA Apt! Steps to Lake with Gym & Parking
The Picasso: #1 Chicago Location
Grace Place in Wrigleyville
Historic oasis in the middle of everything.
Andersonville Luxury Pool Escape
Pet-friendly vacation rentals in Chicago
Lovely top floor 2BR/2BA, steps from everything!
Roscoe Village One Bed Lux Apartment Near Wrigley
The Biddle House (#2)
Studio flat in the heart of Chicago's Gold Coast
Stylish 2BR stunner w/ unbeatable location
Executive Apartment on Lake Michigan with parking
Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt
Huge Pet Friendly East Albany Park Apartment
Vacation rentals with jacuzzis in Chicago
Private Coach house near Lincoln Square!
Lux Urban 3BR/3BA Duplex + Parking!
Ukrainian Village 3BR/3BA • Jet Tub, Private Patio
Modern Lux Getaway w/ Hot Tub, Lrg Yard, Parking
Super Paradise+65 Amenities*Downtown 15 Min
Downtown Chicago - Spa Bath, Patio, 3 blocks to L
The Spa of Downtown Whiting
Checkerboard Studio, Private Outdoor Hot Tub, Yard
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $111 | $113 | $131 | $129 | $148 | $155 | $156 | $160 | $144 | $144 | $129 | $123 |
| Avg. temp | 26°F | 30°F | 40°F | 51°F | 62°F | 72°F | 76°F | 75°F | 68°F | 55°F | 42°F | 31°F |
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 9,630 vacation rentals in Chicago
Verified guest reviews
Over 596,100 verified reviews to help you choose
Family-friendly vacation rentals
4,910 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 3,620 rentals that welcome pets
Vacation rentals with a pool
1,220 properties feature pools
Rentals with dedicated workspaces
6,320 properties have a dedicated workspace
Wi-Fi availability
9,480 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
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- The Field Museum
- Guaranteed Rate Field
- Union Park
- Lincoln Park Zoo
- University of Chicago
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- Museum of Science and Industry
- Washington Park Zoo
- Illinois Beach State Park
- Loyola University Chicago
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