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Vacation Rentals in Chicago

Find 8,218 available offers from 25 partners
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Chicago Condo Rental: Enjoy a Fun and Cultural Trip

The historic city of Chicago boasts a fabulous skyline and a profusion of world-class museums, art galleries, jazz clubs, and playhouses. A walk through downtown Chicago will reveal some of the world's best architectural styles: Gothic, classic, modernist, and more.

The winds that blow across Lake Michigan have earned Chicago a nickname as the Windy City. Check in at your Chicago condo and find out what the fuss is all about.

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Vacation rentals with Wi-Fi

Stay connected while traveling and book a Chicago accommodation with high-speed internet.

Apartment  Humboldt Park
Apr 1 - Apr 8
$115 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in Humboldt Park with Yard & Patio

4.5
Excellent (66 ratings)
Humboldt Park, Chicago, Illinois, United States
Internet
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Condo  Lake View
Jul 7 - Jul 14
$415 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Lake View with Patio & Grill

Lake View, Chicago, Illinois, United States
Internet
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Apartment  South Austin
Jun 29 - Jul 6
$111 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Apartment in South Austin

South Austin, Chicago, Illinois, United States
Internet
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Apartments and vacation rentals with a kitchen

Cook up a feast on your next vacation and book a Chicago rental with full kitchen.

Condo  West Loop
Jul 6 - Jul 13
-41%
$491
$289 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Condo in West Loop

4.9
Outstanding (15 ratings)
West Loop, Chicago, Illinois, United States
Kitchen
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Apartment  Lake View East
Jun 23 - Jun 30
$714 per night
Apartment ∙ 16 guests ∙ 4 bedrooms

Charming Rental Apartment in Lake View East with Patio & Grill

5.0
Outstanding (97 ratings)
Lake View East, Chicago, Illinois, United States
Kitchen
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House  Uptown
Apr 22 - Apr 29
$1,150 per night
House ∙ 21 guests ∙ 6 bedrooms

Vacation Home in Uptown with Yard, Patio & Grill

5.0
Outstanding (147 ratings)
Uptown, Chicago, Illinois, United States
Kitchen
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Vacation rentals and apartments with air conditioning

Keep cool during your trip to Chicago and book a vacation rental with air conditioning.

Apartment  Grand Boulevard
Apr 21 - Apr 28
$177 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Beautiful Apartment in Grand Boulevard with Yard

4.2
Very good (11 ratings)
Grand Boulevard, Chicago, Illinois, United States
Air conditioning
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House  Near North Side
Apr 21 - Apr 28
-37%
$549
$346 per night
House ∙ 11 guests ∙ 3 bedrooms

House in Near North Side with Free Garage + City View

5.0
Outstanding (1 rating)
Near North Side, Chicago, Illinois, United States
Air conditioning
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Apartment  West Town
Jul 21 - Jul 28
$255 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Lovely Apartment in West Town with Private Terrace + Magnificent Views

4.9
Outstanding (30 ratings)
West Town, Chicago, Illinois, United States
Air conditioning
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Best Vacation Home Deals in Chicago

Save up to 48%

House Near North Side
Apr 21 - Apr 28
-48%
$285
$149 per night
House ∙ 10 guests ∙ 2 bedrooms

Nice House in Near North Side

5.0
Outstanding (2 ratings)
Near North Side, Chicago, Illinois, United States
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Condo Roscoe Village
May 21 - May 28
-40%
$383
$231 per night
Condo ∙ 10 guests ∙ 4 bedrooms

Condo in Roscoe Village

3.7
Good (32 ratings)
Roscoe Village, Chicago, Illinois, United States
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Apartment Heart of Chicago
Apr 22 - Apr 29
-42%
$556
$321 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Lovely Apartment in Heart Of Chicago with Patio

5.0
Outstanding (2 ratings)
Heart of Chicago, Chicago, Illinois, United States
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Compare and find a rental that fits your needs among the 8,218 beautiful properties from several vacation rental websites in Chicago. HomeToGo instantaneously highlights the best offers by comparing all of the listed vacation rentals in Chicago from 25 different providers.

Recommended Vacation Rentals in Chicago

Find your perfect vacation rental in Chicago: from $86 per night

House Noble Square
May 4 - May 11
$739 per night
House ∙ 12 guests ∙ 5 bedrooms

Vacation Home in Noble Square with Patio, Yard & Grill

5.0
Outstanding (96 ratings)
Noble Square, Chicago, Illinois, United States
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Condo West Town
Apr 21 - Apr 28
$299 per night
Condo ∙ 9 guests ∙ 2 bedrooms

Condo in West Town with Private Terrace + Skyline View

5.0
Outstanding (207 ratings)
West Town, Chicago, Illinois, United States
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Condo Rogers Park
Oct 27 - Nov 3
$168 per night
Condo ∙ 8 guests ∙ 3 bedrooms

Condo in Rogers Park with Rear Garden

4.9
Outstanding (221 ratings)
Rogers Park, Chicago, Illinois, United States
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Apartment Park Manor
May 21 - May 28
$138 per night
Apartment ∙ 8 guests ∙ 4 bedrooms

Rental Apartment in Park Manor with Yard & Patio

4.9
Outstanding (7 ratings)
Park Manor, Chicago, Illinois, United States
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Apartment West Town
Jun 29 - Jul 6
$280 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Beautiful Apartment in West Town

5.0
Outstanding (9 ratings)
West Town, Chicago, Illinois, United States
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Apartment Portage Park
Apr 21 - Apr 28
$95 per night
Apartment ∙ 10 guests ∙ 3 bedrooms

Family Friendly Private Apartment in Portage Park with Yard, Grill & Patio

5.0
Outstanding (104 ratings)
Portage Park, Chicago, Illinois, United States
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Apartment Roscoe Village
Apr 21 - Apr 28
$200 per night
Apartment ∙ 6 guests ∙ 3 bedrooms

Rental Apartment in Roscoe Village

5.0
Outstanding (6 ratings)
Roscoe Village, Chicago, Illinois, United States
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House West Town
May 21 - May 28
$281 per night
House ∙ 10 guests ∙ 3 bedrooms

House in West Town with Grill & Patio, Queen Sofabed

4.8
Outstanding (50 ratings)
West Town, Chicago, Illinois, United States
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Apartment West Town
Jul 13 - Jul 20
$294 per night
Apartment ∙ 8 guests ∙ 3 bedrooms

Wonderful Apartment in West Town with Yard & Patio

West Town, Chicago, Illinois, United States
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Budget-friendly Vacation Rentals in Chicago

Find Fantastic yet Inexpensive Offers

Apartment Heart of Chicago
May 21 - May 28
-38%
$287
$177 per night
Apartment ∙ 6 guests ∙ 2 bedrooms

Apartment in Heart Of Chicago with Free Parking

4.4
Very good (20 ratings)
Heart of Chicago, Chicago, Illinois, United States
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House Lincoln Park
Apr 22 - Apr 29
$420 per night
House ∙ 24 guests ∙ 4 bedrooms

Vacation Home in Lincoln Park with Grill, Patio & Yard

5.0
Outstanding (168 ratings)
Lincoln Park, Chicago, Illinois, United States
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House Goose Island
Apr 25 - May 2
$220 per night
House ∙ 14 guests ∙ 3 bedrooms

Charming Vacation Home in Goose Island with Sauna, Grill & Patio

4.9
Outstanding (48 ratings)
Goose Island, Chicago, Illinois, United States
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Top-Rated Rentals and Accommodations in Chicago

Book Vacation Rental Offers with the Highest User Rating

House Avondale
Aug 1 - Aug 8
$758 per night
House ∙ 14 guests ∙ 5 bedrooms

Pleasant House in Avondale with Patio, Grill & Yard

4.6
Excellent (54 ratings)
Avondale, Chicago, Illinois, United States
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Condo Rogers Park
Apr 1 - Apr 8
$142 per night
Condo ∙ 6 guests ∙ 2 bedrooms

Spacious Condo in Rogers Park with Private Garden

4.9
Outstanding (191 ratings)
Rogers Park, Chicago, Illinois, United States
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House Woodlawn
Aug 1 - Aug 8
$237 per night
House ∙ 8 guests ∙ 3 bedrooms

House in Woodlawn with Yard & Patio

5.0
Outstanding (2 ratings)
Woodlawn, Chicago, Illinois, United States
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Popular Rental Amenities in Chicago

  • WiFi (7,765)
  • Pool (2,144)
  • Parking (1,016)
  • Pet-friendly (2,258)
  • Kitchen (4,547)
  • TV (7,472)
  • Air conditioning (7,819)
  • Balcony/patio (2,200)
  • Washing machine (4,513)
  • Microwave (4,237)
  • Hot tub (342)
  • Fireplace (1,148)

Use filters to search and find an offer matching your criteria among the 8,218 rentals in Chicago. In Chicago, 7,765 properties provide "Internet". Consequently, if you need internet access during your vacation, select the Internet filter to compare these accommodations. Not as many accommodations in Chicago are available if you want a rental with a sauna or if you need a crib for your baby as "Crib" and "Sauna" are not often available in this destination.

Price and Availability Index in Chicago

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Vacation Rental Price Information in Chicago

This graph displays average prices of the vacation rentals and holiday apartments located in Chicago. $551 is the highest price average in the next twelve months. On the other hand, in March you will find the cheapest prices (3/22 – 3/29). Prices this week are on average $124 a night.

Rental availability information in Chicago

Check how busy Chicago is with our availability graph. So far, the week with the least available rentals in Chicago is in March (3/22 – 3/29). People tend to travel less to Chicago during a week in June (6/29 – 7/6) when only 35% of the rentals are booked.

The Weather in Chicago

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- Rainy days

Find the Chicago climate diagram. On average, the warmest month is July. On the contrary, the coolest month is January. The rainiest month is March while the driest month is February.

7-Day Weather Forecast in Chicago

Wed, 24 Apr
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6 h

11 mi/h

Thu, 25 Apr
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Fri, 26 Apr
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Sat, 27 Apr
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16 mi/h

Sun, 28 Apr
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17 mi/h

Mon, 29 Apr
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Tue, 30 Apr
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Accommodations for your vacation in Chicago

In Chicago, many of the 8,218 property types are apartment rental, which represent 64.87% of its accommodations being offered. Additionally, the average nightly price of apartment rental in Chicago is $341, and the median size is 85 m². Moreover, the majority of apartment rental in Chicago can host 4 people, which makes it a wonderful vacation spot for medium-sized groups and families. House rental are the other most frequent property type in Chicago. These properties cost $652 per night on average and have an average size of 145 m².
Where to find the best food in Chicago?

The 5 Best Brunch Places with Awesome Coffee

1. All Together Now

Have a relaxed weekend brunch at All Together Now, a bottle shop and all-day café. Dig into creamed eggs over toast with pork fat collards or choose to build your own meat and cheese board. As for the coffee, the beans come courtesy of the revered Ruby Coffee Roasters.

2. Cafe Marie-Jeanne

If you are looking for delicious French fare and excellent coffee, Cafe Marie-Jeanne ticks all the boxes. Popular for its deli counter treats and Chicago-style lobster rolls, this eatery also serves indulgent French pastries. Ask for the bottomless coffee or cold brew.

3. Beatrix

At Beatrix, you can choose a healthy brunch of quinoa cakes with poached eggs or treat yourself to fresh chocolate chip cookies. At the coffee bar, there are several options for your caffeine fix, ranging from iconic local roasters like Metric to Mexican iced coffee.

4. Dollop Diner

At Dollop Diner, coffee is elevated to an art form, much to the delight of locals. Choose your brew and savor it along with chicken and waffles or fluffy buttermilk pancakes. The seats by the large windows are ideal for people watching to complete the laid-back brunch experience.

5. M. Henry

Brunching at M. Henry means prompt refills of the yummy Metropolis house blend. Pair it with the much-loved peach and sour cherry brioche French toast or go for the comfort brunch plate. The café is BYOB, which is yet another cherry on the cake.

What is the weather like in Chicago?

A Good Time to Visit

The best time to visit Chicago is in spring and fall, when the weather is pleasant and prices of vacation rentals are reasonable. Moreover, plenty of cultural activities take place in those seasons. If you intend to visit during summer, book your accommodation well in advance, as this is the most popular visiting season. Chicago can be just as magical in winter, making it a true year-round city.

What are the top sights in Chicago?

The Best Neighborhoods in Chicago

Chicago's international neighborhoods are so true-to-life, you'd be forgiven for thinking you were genuinely in another country. There's Chinatown, the Korean community in Lawrence Avenue, the Swedish settlement at Andersonville, Little Italy, Greektown, and several other international pockets. The Polish Cathedrals of St. Mary of the Angels in Bucktown and St. Hyacinth Basilica in Avondale are exquisite. Experience the different facets of the city with guided architecture walks or a river boat tour.

The world comes to Chicago for gastronomical expertise, so indulge those taste buds! Devon Avenue is the place for Indian delights, and a mix of everything is served in Uptown, including American, Ghanaian, Nigerian, Japanese, and even Swedish delicacies.

Chicago is a drinking city that is home to a record number of dive bars, lounges, and breweries, the best of them found in the Logan Square and Bucktown areas.

What are the best places to discover the arts and culture of Chicago?

Art and Culture in the City

Art and history enthusiasts will have plenty of choice with the variety of art galleries and museums scattered across the city. The Art Institute of Chicago in the Loop district houses priceless Impressionist and Modernist works, and there's also the National Museum of Mexican Art in Pilsen, the Museum of Photography, the Polish Museum of America in Wicker Park, the International Museum of Surgical Science, and more. Buy the Chicago CityPASS to save money if you plan on visiting several attractions in a short span of time.

For improvisational comedy and performance art, catch a show at The Annoyance Theater, I.O., or the Playground. Steppenwolf in Lincoln Park is more serious, having hosted the likes of John Malkovich. Visit the Auditorium in the Loop for its architecture and brilliant use of performance space. For rock, blues, jazz, and spoken-word performances, the Chicago Theater awaits.

What are the best activities for families in Chicago?

Activities with Children

Chicago has plenty to keep kids occupied. Right along the lake on Museum Campus lie three institutions within walking distance of each other. The Adler Planetarium has the coolest astronomy shows and exhibits, while the Shedd Aquarium features majestic sharks, dolphins, whales, and other superb marine life. The kids will love the giant Tyrannosaurus Rex skeleton in the Field Museum of Natural History. How about a picnic on the clean shores of Lake Michigan to finish up? The waters are safe and excellent for swimming.

What are the best nightlife spots in Chicago?

The 5 Best Bars in Chicago with a View

1. Cindy's

Cindy's, the hip bar on the Chicago Athletic Association Hotel rooftop, overlooks Lake Michigan and provides spectacular views of Millennium Park. The picnic-style seating and artisan cocktails combined with the stylish ambiance make it just the bar for a relaxed evening with friends or a special someone.

2. Drumbar

Drumbar, one of the favorite night spots in Chicago, is known for its creative craft cocktails. The 18th-floor rooftop lounge and bar welcomes guests with refreshing views of Lake Michigan. Take your pick from the extensive bar menu and unwind on the lovely, breezy terrace complete with warming fire pits.

3. Terrace 16

Visit Terrace 16 at the Trump International Hotel & Tower Chicago for its views of the point where Lake Michigan meets the Chicago River. Enjoy the evening as you sip on specialty cocktails and indulgent bar bites like truffle fries. The Wrigley Building Clock Tower is also within eyesight of this upscale bar.

4. J. Parker

Beautiful scenery throughout the year coupled with soothing views of Lincoln Park and the boats on Lake Michigan make the J. Parker another popular bar with a view in the city. The swanky lounge serves handcrafted cocktails with gourmet small plates and New American fare to accompany your drink.

5. Waydown

Head to the Waydown for a round of drinks in a stylish setting complete with live music. The two outdoor patios and excellent views of the city make this Scandinavian-chic bar perfect for lounging in an open-air space. Cocktails created by the celebrated Caitlin Laman are another reason to visit.

Where are the unique attractions in Chicago?

3 Great Day Trips from Chicago

The city’s location makes it convenient to explore neighboring destinations on short day trips. Just a 90-minute drive will take you to Milwaukee, a city known for its breweries. The Milwaukee Public Museum, Discovery World, and Harley-Davidson Museum are popular attractions in this Wisconsin city.

Get more out of your stay at a Chicago vacation house with a trip to Starved Rock State Park. A delight for outdoor enthusiasts, this park is known for the many sandstone canyons that were created by glacial meltwater. Explore the different hiking trails through lush green areas and spend time by the waterfalls.

Another worthwhile trip is to Michigan City, just an hour away from Chicago. Spend the day visiting popular attractions like Washington Park, the Old Lighthouse Museum, and the gorgeous Barker Mansion. Family vacationers can visit the zoo and later hit the beach area for some boating, surfing, and swimming.

What are the best events and festivals in Chicago?

Regular Events and Festivities

The year begins with colorful Chinese New Year celebrations and the highly-awaited Chicago Auto Show. April brings the Chicago Improv Festival and C2E2 Chicago Comic & Entertainment Expo. The summer months are chock-full with events, including the Puerto Rican Parade & Festival, Chicago Blues Festival, and Chicago Pride Fest in June, followed by the Square Roots Festival in July, and Lollapalooza and the Chicago Jazz Festival in August.

Film lovers and athletes should watch out for the Chicago International Film Festival and the Chicago Marathon in October. The year ends on a whimsical note with Christkindlmarket, the Magnificent Mile Lights Festival, and the Winter WonderFest at Navy Pier, where the entire city is adorned with lights.

Book a Chicago condo rental for an unforgettable time in the Windy City!

What are the must-see attractions in Chicago?

6 Must-See Attractions in Chicago

1. 360 Chicago Observation Deck

What better to way to see the city than from above? Travel up to the 94th floor of the John Hancock Center for stunning views of the city and over Lake Michigan.

2. Lincoln Park Zoo

The city's most popular attraction, this iconic zoo houses African apes and other interesting species. Be sure to allow for plenty of time to explore its plentiful and varied exhibits!

3. Museum of Science and Industry

At this world-class interactive museum, you'll find a life-size replica coal mine and recreated historic Chicago streets, with functional shops and other interesting querks.

4. Cloud Gate

One of the most iconic pieces of art in the United States, Cloud Gate was created by Anish Kapoor. This beautiful reflective sculpture is nicknamed 'The Bean' due to its shape, and attracts photographers from across the world.

5. Millennium Park

This majestic urban park in the center of Chicago is a great place to wile away an afternoon amidst a tranquil backdrop. Concerts, local fairs, and fun events are held regularly at the park.

6. Art Institute of Chicago

As one of the oldest and largest galleries in the country, this impressive museum showcases over 300,000 artworks. Modern art, photography, and ancient sculptures are all on display for visitors to enjoy.

Information about vacation rentals in Chicago

🏡 Vacation rentals available 8,218 rentals
💳 Possible discounts up to 40%
🌙 Nightly prices starting at $86
⭐ Popular amenities Internet, Pool and Parking
🐾 Pet friendly homes 2,258 homes
🏊 Vacation rentals with pools 2,144 homes
9 reviews
Chicago vacation rentals have an average rating of 4.6/5 on 9 reviews left by travelers.

Frequently Asked Questions

What is the typical nightly price for a vacation home in Chicago?

The nightly price of accommodations in Chicago starts at $86. If you are looking for a apartment rental, the nightly price is $341 on average. A house rental Chicago will cost on average $652 per night.

How many vacation rentals are available to book in Chicago?

There are 8,218 rentals from 25 providers in Chicago.

What are the most popular amenities for vacation rentals in Chicago?

If you're looking to book a vacation rental in Chicago, the most popular amenities are: Pool, Internet and Parking.

How many vacation homes with pools are in Chicago?

Chicago has 2,144 Hotel room and Apartment rental on offer to book.

Are dogs allowed in vacation homes in Chicago?

If traveling with a pet in Chicago, 27% of rentals are pet-friendly.

What's the best time of year to travel to Chicago?

Chicago has its warmest time of year around July and August, with average prices of $86 per night.

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