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Vacation rentals in Chicago

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Quick stats about vacation rentals in Chicago

  • Total vacation rentals

    Explore 10,070 vacation rentals in Chicago

  • Verified guest reviews

    Over 621,830 verified reviews to help you choose

  • Family-friendly vacation rentals

    5,020 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 3,570 rentals that welcome pets

  • Vacation rentals with a pool

    1,250 properties feature pools

  • Rentals with dedicated workspaces

    6,410 properties have a dedicated workspace

  • Wi-Fi availability

    10,010 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

  • 4.8 Average rating

    Chicago stays are highly rated by guests—averaging 4.8 out of 5!

  • Nearby attractions

    Chicago's top spots, include Millennium Park, Wrigley Field, and Lincoln Park

Top-rated vacation rentals in Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.
Apartment in West Rogers Park

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

LocationFamilyOutdoor spaces

4.99 out of 5 average rating, 118 reviews
Top guest favorite
Apartment in Oak Park

Oak Park Space+Style Duplex Parking+Walk to Train

A warm, curated home with two floors of living space. Perfect for families with kids, groups of friends and multi-generational living. The main floor + finished basement total 3 bdrms + 2.5 baths. Primary suite is on the main floor. Two secondary bedrooms are on the lower w/ a full bath. 20 min to downtown Chicago. Walk to dining + train+ FLW Home. Open living/dining/kitchen/sunroom. Remote work space. Coffee bar. Private entry/deck. Driveway parking. Central AC. Upstairs apartment is separate.

FamilyValueKitchen

5.0 out of 5 average rating, 104 reviews
Top guest favorite
A private outdoor patio is surrounded by wooden fencing, featuring a glowing sofa and two chairs placed on a patterned rug. A small table holds a plant, while greenery adds a natural touch to the tranquil setting, under a colorful sky at dusk.
Home in Chicago

The Chicago River House – GIANT wall projector!

Close to must see Chicago restaurants and nightlife, yet nestled in nature! This 1937 Print Shop is seated between the Chicago River & Forest Preserves, with trails & river walks, 3 miles to the beach, near Lake Shore Drive & 90/94, nearby Lincoln Square , Andersonville, and seasonal waterfalls, brunch nearby. This 2-bed, 2-bath home one level. 5star Chef's kitchen 9’ x 15’ HD projector, comfy beds, double shower head shower room, near nature. Relax on our private patio and glowing furniture

FamilyValueQuiet

4.96 out of 5 average rating, 213 reviews
Top guest favorite
Apartment in Logan Square

Paradise on the Boulevard!

Amazing 2 bedroom garden apartment, located in the heart of the highly desirable Logan Square. This luxurious space with heated polished concrete floors & spa inspired bathroom is situated on the Historic Logan Boulevard, just steps from CTA Blue Line. Fabulous restaurants and coffee shops across the street. The apartment has a private entrance & access to a fabulous shared backyard space. The owner's treehouse deck can be reserved by request. Peace, convenience & excitement are right here.

FamilyValueAccuracy

4.99 out of 5 average rating, 111 reviews
Top guest favorite
A cozy seating area features a green sectional sofa adorned with decorative pillows in various patterns. A small wooden coffee table sits at the center, topped with a book and a small plant. Exposed brick walls complement large windows dressed with dark curtains.
Condo in Wicker Park

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

LocationFamilyAmenities

4.98 out of 5 average rating, 170 reviews
Guest favorite
An open living and dining area features neutral-colored walls and natural light from multiple windows. A spacious white sofa is positioned across from a mounted television. A modern dining table is accompanied by four chairs, while a closet and laundry unit are neatly integrated into the space.
Apartment in Downtown Chicago

Beautiful 2BR Apartment in Old Town

Want to experience Chicago neighborhood charms, there is no better place to start than the Old Town Historic District. This 2 bedroom apartment is part of a Victorian-era building while interior has been updated for modern style living. You can enjoy lake front trail in the Summer, Bears football in the Fall, year end holiday shopping in the Winter, and Blackhawks playoffs in the Spring. With both Red and Brown line only a few blocks away, getting around in Chicago does not get any easier.

ValueFamilyGetting around

4.89 out of 5 average rating, 307 reviews
Guest favorite
A spacious living room features large windows allowing natural light. A modular sectional sofa is arranged invitingly in front of a sleek fireplace. A modern coffee table sits atop an area rug with geometric patterns, and an expansive wall-mounted TV awaits entertainment.
Home in Chicago

Gorgeous 5 BR Gem Sleeps 18 with Tons of Games!

No cleaning fees! Gorgeous gem 10 miles from Downtown, Airport, Lake Michigan, and United Center! 15 miles from Wrigley Field and the Zoo. Next to CTA! 6 bedrooms 2 bathrooms, 10 beds. Sleeps 18 comfortably. Perfect for large groups! Modern smart home with air hockey, pool table, video games, 2 ping pong tables, foosball, 9 big screen TVs including 85" Samsung QLED with surround sound, outdoor dining, charcoal grill, cornhole, dining room, game room, 2 living rooms, and full kitchen.

FamilyValueCheck-in

4.91 out of 5 average rating, 136 reviews
Guest favorite
Apartment in Downtown Chicago

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!

FamilyValueAccuracy

4.9 out of 5 average rating, 126 reviews
Superhost
A serene bedroom features a spacious bed with crisp white linens and a light gray upholstered headboard. Natural light flows through large windows, illuminating the neutral walls and wood flooring. A small bedside table with a decorative lamp adds a touch of elegance to the space.
Apartment in Downtown Chicago

Kasa | Views from your Private Balcony | 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.

FamilyValueCondition

4.81 out of 5 average rating, 1052 reviews
Top guest favorite
A contemporary loft bedroom features a spacious bed with a light grey quilt. Exposed brick walls complement framed vintage Chicago artwork. Soft lighting is provided by string lights near the window. A green plant adds a touch of nature, while dark wood accents create warmth.
Loft in Lake View

Lakeview Loft-Vintage Chicago, Modern Amenities

The Lakeview Loft is a freshly remodeled loft space with a vintage Chicago theme and modern amenities. Located in the Lakeview neighborhood, it is 1/2 mile to the Brown & Red Line el trains, less than a mile to Wrigley Field and 1.5 miles to the lakefront. The Lakeview Loft will provide guests a true Chicago experience while staying in a great Chicago neighborhood. We believe in giving back to our neighborhood as well so for each booking we donate $5 to a local children's charity.

ValueFamilyCleanliness

4.96 out of 5 average rating, 608 reviews
Top guest favorite
A light-filled living area features a gray sectional sofa adorned with blue and yellow cushions. Two large windows provide perspectives of the outdoors. A world map hangs on the wall, complemented by a small coffee table and a patterned area rug, contributing to a cozy setting.
Apartment in Lincoln Park

Explore Lincoln Park from a Polished Apartment

A bright, cozy, large studio in the heart of Lincoln Park! You enter with a keypad code which we give you a few days prior to your stay. You are steps away from Armitage Ave. and Halsted St. for walkable grocery stores, shops, restaurants and cafes, plus Red and Brown line train stations that access Downtown and other parts of the city. Street parking is relatively easy around the apartment with free residential parking stickers or an onsite garage space for $25/night.

LocationFamilyParks

5.0 out of 5 average rating, 325 reviews
Guest favorite
A modern living area features a large dark sofa and a glass coffee table atop a geometric patterned rug. Oversized windows provide views of the city and lake. A small dining area with sleek chairs and tropical plants adds a touch of greenery to the space.
Apartment in Downtown Chicago

Modern Corner 2BR in Streeterville | Roof Deck | L

Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple directions. This bright and modern two bedroom, one bathroom corner unit is perfect for travelers looking for a stylish escape in the sky in downtown Chicago just off the Magnificent Mile and the lakefront. The building has great amenities including an amazing rooftop terrace with 360 degree views of the skyline and the lake. This is the best location in the city!

FamilyValueHeating

4.77 out of 5 average rating, 217 reviews

Popular amenities for Chicago vacation rentals

Self check-inMonthly staysLake accessFree parking on premisesGym

Stay near Chicago's top sights

Wrigley Field

2,208 locals recommend

O'Hare International Airport

149 locals recommend

Soldier Field

349 locals recommend

Navy Pier

2,055 locals recommend

Millennium Park

1,673 locals recommend

Lincoln Park Zoo

2,512 locals recommend

Private Chicago vacation rentals

Top guest favorite
The living area features exposed brick walls, contributing to a vintage feel. A cozy sofa is positioned next to a wooden coffee table, while a television is mounted on a rustic console. Natural light enters through two windows, covered with light blinds.
Apartment in Logan Square

Bucktown Brick Cottage Apartment

LocationValueLayout

4.98 out of 5 average rating, 174 reviews
Superhost
A spacious studio is showcased with a king-size bed positioned against a contrasting dark wall. Natural light filters through large windows, highlighting the exposed brick and the vintage stone fireplace. A mirrored wall accents the room, while a desk complements the seating area.
Condo in Little Italy

Private hot tub - King bed suite - Free parking

FamilyValueSolo travel

4.92 out of 5 average rating, 283 reviews
Top guest favorite
A comfortable living area is highlighted by a mix of seating options, including a gray sofa with patterned pillows and blue accent chairs. A round wooden coffee table sits on a soft rug, while a map-themed wall art adds character. The open layout connects to the kitchen area.
Apartment in Downtown Chicago

Unwind in Style Steps from the Magnificent Mile

ValueFamilyLayout

4.98 out of 5 average rating, 443 reviews
Top guest favorite
A dining area features a wooden table with seating for four, positioned against a textured brick wall. Two windows allow natural light to fill the space, with sheer curtains gently framing them. A vibrant green plant and neon 'CHICAGO' sign add character to the room.
Apartment in Wicker Park

【Central】- Eclectic Fun 1BR APT in Wicker Park

LocationValueKitchen

4.95 out of 5 average rating, 168 reviews
Top guest favorite
A modern kitchen and dining area are highlighted by sleek white cabinetry and stainless steel appliances. A spacious island with two stools provides seating, while a wooden dining table accommodates four. A decorative shelving unit displays various items, enhancing the clean aesthetic.
Apartment in Lincoln Park

Luxury 2-story 2-bedroom 3-bath Lincoln Park Apt

LocationFamilySleep quality

4.99 out of 5 average rating, 166 reviews
Superhost
Condo in Ukrainian Village

Modern Chicago Movie Themed Apt

FamilyValueHospitality

4.88 out of 5 average rating, 229 reviews
Top guest favorite
A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.
Apartment in Lake View

Chic retreat near the best of Lakeview & Wrigley

FamilyLocationLaundry

4.93 out of 5 average rating, 196 reviews
Top guest favorite
The modern kitchen features navy blue cabinetry and a central island with seating for three. Stainless steel appliances include a refrigerator, stove, and dishwasher. Pendant lighting hangs above the island, and a window provides natural light, complementing decorative wall art.
Apartment in Wicker Park

Stylish 2BR stunner w/ unbeatable location

LocationFamilyCondition

4.92 out of 5 average rating, 207 reviews

Vacation rentals with pools in Chicago

Guest favorite
A spacious bedroom features large floor-to-ceiling windows, allowing natural light to fill the room. A large bed with neutral bedding is complemented by a contemporary desk and chair setup, which is arranged near a wood-framed lamp. A subtle area rug lies beneath the bed.
Apartment in Downtown Chicago

50th Floor Mag Mile Views, Balcony, Pool, Gym

LocationValueCheck-in

4.9 out of 5 average rating, 143 reviews
Guest favorite
Apartment in Downtown Chicago

Gold Coast Luxury: 2BR with Sweeping City Vistas

FamilyValueLong stay

4.94 out of 5 average rating, 126 reviews
Top guest favorite
An aerial view of a swimming pool surrounded by a spacious wooden deck. Six comfortable loungers are positioned around the pool, with additional seating areas visible. An umbrella-covered table is set for outdoor dining, harmonizing with the greenery in the yard.
Apartment in Logan Square

Fun & cozy getaway w/POOL/game room/FREE parking

LocationValueQuiet

4.98 out of 5 average rating, 172 reviews
Guest favorite
A large outdoor pool is surrounded by a modern deck featuring lounge chairs. High-rise buildings provide a city backdrop against a clear blue sky.
Apartment in Downtown Chicago

Highrise Hideout (Fitness Center • Sauna)

FamilyValueCheck-in

4.91 out of 5 average rating, 123 reviews
Guest favorite
A cozy bedroom features a spacious bed dressed in bold black and white striped bedding. A decorative red pillow adds a pop of color. A framed artwork of a rabbit is displayed above the bed, complemented by bedside tables with a lamp and a small potted plant.
Apartment in Uptown

Whole Flat in Private Club. Walk to L, Dining & Shows

LocationFamilyParks

4.9 out of 5 average rating, 600 reviews
Top guest favorite
An open-concept living area features large windows that invite natural light and provide a view of the cityscape. A comfortable blue sofa is adorned with patterned pillows, while a light wood coffee table sits in front of it. A dining space with black chairs complements the modern kitchen.
Condo in Evanston

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

FamilyValueLaundry

4.96 out of 5 average rating, 141 reviews
Guest favorite
The modern kitchen features white cabinetry and a spacious island with four bar stools. A stainless steel refrigerator stands next to a gas stove and microwave. Natural light filters through large windows, illuminating the elegant countertops and sleek finishes.
Apartment in West Town

Cozy Duplex Down in Wicker Park East w/ Parking

FamilyLocationTV

4.93 out of 5 average rating, 131 reviews
Guest favorite
The living area features a comfortable gray sofa facing a modern TV stand. A light rug lies beneath a white coffee table adorned with a small plant. Natural light filters through a large window, complemented by soft curtains. A desk and chair are positioned in the corner.
Condo in Elk Grove Village

Just remodeled apartment close to airport and mall

ValueFamilyLaundry

4.92 out of 5 average rating, 127 reviews

Vacation rentals with jacuzzis in Chicago

Guest favorite
The exterior of a charming coach house is presented, featuring wooden shingles and a well-maintained yard. A circular table with chairs is set on the lawn, accompanied by a green umbrella for shade. Lush bushes border the property, and a wooden fence encloses the yard.
Guesthouse in Chicago

Private Coach house near Lincoln Square!

LocationFamilyOutdoor spaces

4.88 out of 5 average rating, 397 reviews
Top guest favorite
A modern kitchen features a large stainless steel island with seating for three. Black cabinetry offers ample storage space, complemented by open shelves displaying various kitchen items. Pendant lights hang above, illuminating a stylish workspace adorned with greenery, while industrial elements add character.
Loft in Wicker Park

Tea Studio in Wicker Park Spring Factory

LocationValueSleep quality

4.96 out of 5 average rating, 309 reviews
Top guest favorite
An outdoor space is showcased featuring a hot tub under a pergola with string lights, providing a relaxed ambiance. Comfortable seating is arranged around a firepit table, complemented by a gas grill visible in the background.
Home in Bridgeport

Modern Getaway w/ Hot Tub, Lrg Yard, Parking

FamilyValueNearby

4.96 out of 5 average rating, 187 reviews
Guest favorite
An open and spacious living area features a white sectional sofa and unique cow print coffee table. The dining space is equipped with round chairs, and a modern kitchen is visible in the background. Light streams through frosted glass block windows, enhancing the airy atmosphere.
Apartment in West Town

Checkerboard Studio, Private Outdoor Hot Tub, Yard

FamilyLocationBathroom

4.86 out of 5 average rating, 540 reviews
Guest favorite
A spacious living room features comfortable seating on soft gray furniture, including a large chaise and armchairs. Natural light brightens the area, while a gas fireplace is set within a stylish stone surround. A large flat-screen TV is mounted above the fireplace.
Home in Lake View

Entire house in Lakeview with yard and garage

ValueLocationWalkability

4.86 out of 5 average rating, 111 reviews
Top guest favorite
An elegantly furnished dining area features a wooden table with a textured runner. Dark leather chairs surround the table, and a modern chandelier hangs above. The open kitchen, equipped with stainless steel appliances and bar seating, is visible in the background.
Condo in Logan Square

Urban Luxury 1BR/2BA Logan Square Condo w/Garage

ValueFamilyQuiet

4.98 out of 5 average rating, 329 reviews
Guest favorite
A spacious living room features a rich blue accent wall and mid-century modern furniture. Two armchairs and a plush sofa are arranged around a low coffee table. A television is mounted on the wall, complemented by decorative wall art. Natural light fills the room.
Home in Westchester

Modern 2Bdrm Westchester/Chicago Home.With Hot tub

FamilyLocationKitchen

4.87 out of 5 average rating, 103 reviews
Top guest favorite
The living area features a spacious couch accompanied by two armchairs, all positioned around a circular dining table. A large window allows natural light to illuminate the space, adorned with potted plants and modern artwork that adds a touch of style.
Condo in Ukrainian Village

Ukrainian Village 3BR/3BA • Private Patio, Parking

LocationFamilyCheck-in

4.98 out of 5 average rating, 128 reviews

When is the best time to visit Chicago?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$23,206 GYDG$23,624 GYDG$27,387 GYDG$28,641 GYDG$34,704 GYDG$38,467 GYDG$32,613 GYDG$33,449 GYDG$30,104 GYDG$30,104 GYDG$26,969 GYDG$25,714 GYD
Avg. temp-3°C-1°C4°C10°C16°C22°C25°C24°C20°C13°C6°C0°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.

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