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Holiday houses in Chicago

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Quick stats about holiday rentals in Chicago

  • Total holiday rentals

    Explore 10,070 holiday rentals in Chicago

  • Verified guest reviews

    Over 621,830 verified reviews to help you choose

  • Family-friendly holiday rentals

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

  • Pet-friendly accommodation

    Find 3,570 rentals that welcome pets

  • Holiday 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 holiday 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 holiday rentals in Chicago

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

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Top Guest favourite
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.

4.99 out of 5 average rating, 122 reviews
Guest favourite
Home in South Side

Luxury 4BR w/ Spa Tub Near UChicago & Obama Center

Discover Metra Haven, a luxury thoughtfully designed 4BR near Hyde Park, this home is ideal for bachelorette weekends, girls trips, family gatherings, professionals or large groups seeking cozy comfort Unwind in the spa-style bath tub, gather in the private backyard patio, with fire place for cozy evenings accommodating your group Steps from Metra station with a direct train to Downtown, 4mins away from the Obama presidential center in Jackson pack, museum of science & industry and the lake

4.92 out of 5 average rating, 39 reviews
Apartment in Downtown Chicago

Kasa Lake Shore Chicago | Two Bedroom King & Queen

Kasa Lake Shore Chicago offers spacious, furnished apartments for short and extended stays, steps from Lake Michigan, Navy Pier, and the Magnificent Mile. Each tech-enabled unit has a full kitchen, in-unit laundry, and access to co-working areas, offering more space than a hotel for business and leisure travelers. Check-in starts at 4pm and can be done contactless from your phone, or in person at our front desk, open daily from 11am to 730pm. Text us anytime for Virtual Front Desk support.

4.64 out of 5 average rating, 36 reviews
Top Guest favourite
Home in Humboldt Park

Beautifully Renovated Loft-Style Coach House

Stay at this beautifully renovated all-brick coach house in lovely Humboldt Park/West Town! Once a cigar factory in 1908, this unique space has been fully rehabbed & restored for a charming and industrial stay. Its an open-concept loft-style house, and is entirely private - no neighbors above or below you. It boasts a balcony and a large rooftop deck with gorgeous city skyline views. We are proud to be a family-owned rental and take care and pride in this special space! Welcome to Chicago!

5.0 out of 5 average rating, 40 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.

4.81 out of 5 average rating, 1064 reviews
Hotel room in The Loop

Central Loop Hotel, Standard room

After a day of exploring the city, unwind in your spacious standard room featuring premium bedding and thoughtfully placed charging points. Stay productive with a multipurpose workspace, ergonomic chair, and task lighting, or relax with lightning-fast free Wi-Fi and a flat-screen smart TV. Enjoy a Nespresso brewer with complimentary coffee and tea, plus in-room yoga mat and resistance bands for your wellness. Bathroom amenities include C.O. Bigelow products, toiletries & hair dryer.

4.64 out of 5 average rating, 384 reviews
Top Guest favourite
Apartment in South Side

European Coziness in Bronzeville

Brand-new luxury 3BR, 2BA top-floor apartment in the heart of historic Bronzeville. Designed for families, groups, and business travelers, it features stylish interiors, a fully equipped kitchen, spacious living area, and premium finishes throughout. Minutes from McCormick Place (3.4 mi), Downtown, Hyde Park, museum of Science and Industry, University of Chicago, and the lakefront. Experience comfort, space, and one of Chicago's most vibrant neighborhoods.

5.0 out of 5 average rating, 15 reviews
Superhost
Home in Bensenville

Fun and Cozy Family Home Near O’hare Airport

Spacious, amenity-filled home just minutes from O’Hare Airport, perfect for families and groups. Private 2-car garage plus driveway parking included. Sleeps many with 1 king bed, 3 queen beds, a twin-over-full bunk bed, and 3 twin futons. Enjoy 4 full baths, including a master jacuzzi, closets in every bedroom, and a fully equipped kitchen with coffee bar. Entertainment includes a theater room, gym, ping pong, 4-in-1 game table, and board games.

4.89 out of 5 average rating, 27 reviews
Guest favourite
A modern kitchen is showcased, featuring sleek cabinetry in dark tones and stainless steel appliances. An island with a light countertop provides ample space for meal preparation. Natural light enters through large windows, brightening the inviting atmosphere of the open layout.
Apartment in West Side

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

4.95 out of 5 average rating, 138 reviews
Hotel room in The Loop

Arlo Chicago, City king

Step into the city king room where inspiring views of downtown and a spacious cozy king bed invite you to relax in style. Enjoy smart amenities like a Nespresso coffee machine, a 55 inch flat screen TV, a smart fridge and a work desk. Contemporary luxury design and thoughtful details like a hand held steamer hair dryer and laptop sized safe make this a perfect home base whether you are exploring the city or enjoying a quiet night in.

4.78 out of 5 average rating, 176 reviews
Hotel room in Downtown Chicago

Millennium Hotel Knickerbocker Chicago, Standard .

Standard room offers a tastefully decorated space with a plush king bed designed for your comfort and relaxation. Enjoy modern amenities like WiFi, smart TV and an in room safe along with coffee and tea making facilities. Thoughtful touches create a welcoming atmosphere for both work and leisure making it an ideal choice for any traveller. Unwind and recharge in style during your stay.

4.63 out of 5 average rating, 2439 reviews
Hotel room in Downtown Chicago

Riu Plaza Chicago, Deluxe king room

The perfect choice for a relaxing break in the exciting city of Chicago. Includes a shower, hair dryer, central heating, air conditioning, and an in-room safe for your convenience. Enjoy added comforts like a small fridge, coffee maker, and a cozy sofa to unwind. An iron is also provided.

4.82 out of 5 average rating, 33 reviews

Popular amenities for Chicago holiday rentals

KitchenWi-FiPoolFree parking on premisesAir conditioning

Stay near Chicago's top sights

Wrigley Field

2,208 locals recommend

O'Hare International Airport

149 locals recommend

Soldier Field

350 locals recommend

Navy Pier

2,056 locals recommend

Millennium Park

1,673 locals recommend

Lincoln Park Zoo

2,512 locals recommend

Other great holiday rentals in Chicago

Hotel room in West Loop

The Emily Hotel, Deluxe double

4.92 out of 5 average rating, 65 reviews
Hotel room in Downtown Chicago

Level Chicago - River North, Deluxe two bedroom s.

4.67 out of 5 average rating, 9 reviews
Hotel room in Downtown Chicago

The Godfrey Hotel Chicago, Selected by hotel

4.62 out of 5 average rating, 371 reviews
Hotel room in The Loop

Club Quarters Hotel Central Loop, Chicago, Club r.

4.59 out of 5 average rating, 71 reviews
Hotel room in West Loop

Level Chicago - Fulton Market, Studio

4.53 out of 5 average rating, 32 reviews
Hotel room in The Loop

The Royal Sonesta Chicago Downtown, King - city v.

4.72 out of 5 average rating, 232 reviews
Hotel room in Lake View

City Suites Hotel, Queen room

4.64 out of 5 average rating, 87 reviews
Hotel room in Downtown Chicago

Kinzie Hotel, Deluxe king non smoking

4.74 out of 5 average rating, 19 reviews

When is the best time to visit Chicago?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$198 NZD$202 NZD$234 NZD$245 NZD$297 NZD$329 NZD$279 NZD$286 NZD$257 NZD$257 NZD$230 NZD$220 NZD
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.

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