Chicago vacation rentals

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Top-rated vacation rentals in Chicago

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

Guest favorite

Guesthouse in Chicago

4.99 out of 5 average rating, 776 reviews

Polk Street Coach House Apartment, Little Italy/Medical Dist

Cook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs. Welcome to Polk Street Guest House: a well-appointed, completely private, 2-bedroom carriage house in Little Italy near the Medical District. Decorated with mid-century antiques and paintings, our 2nd floor coach house apartment is perfect for guests looking for a home-away-from-home. It has a fully-equipped kitchen, teak furnishings, comfortable queen size beds, and a private entrance accessible though a side gate from the street. For folks with kids, please note there is no child gate near the top of the stairs. Enjoy quiet parks and have easy access to all of Chicago. Major hospitals at Rush, University of Illinois, Hines, VA and Stroger are within 3 to 6 blocks. Chicago's elevated pink line train is 2 blocks away; the Blue line is 3 blocks. Take a quick cab ride to “the loop" downtown for $10, or take a Divvy bike. Chicago's famed Little Italy restaurants on Taylor Street are a block South. Free street parking with 24-hour zoned pass. Your hosts: Ken & Curt Want privacy? You have privacy! Use an entry code to access the coach house through the side gate to the left of our main house. Your private entrance, which also has keypad entry, is on the left side of the vine-covered brick building in back. The main living area is upstairs. There will be a 24-hour zoned parking pass waiting for you on a shelf as you enter the Coach with instructions on how to fill out the parking pass. We regret that the Coach House is not ADA/wheelchair accessible. For those arriving early than check-in, or who are staying later than check-out, we have an area beneath the coach house where you may leave your luggage. Just ask. Our space is your space. The coach house is entirely separate from our main house where we live. The coach house has a separate entrance and full amenities. You’re welcome to use the seating area in the courtyard, and the Weber grill. We're happy to provide any tips about the city, or to help show you how to use anything in the apartment. Just call our cell phones (they are listed in the apartment), or step across the yard and say hello. Three blocks to the Medical District and major hospitals, walk from this tree-lined Little Italy neighborhood to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Indian cuisine on Taylor Street. Stroll in Garibaldi Park on the doorstep, with Arrigo Park a block away. We are conveniently located for transit, bike, car and Uber. Public Transportation: -Pink Line, Polk Station, CTA: 3 blocks west of us, this rail line gets you downtown in 10 minutes (plan 30 minutes total time with walking for most destinations) and is useful for most site-seeing. -Blue Line, Racine Station, CTA: 4 blocks east or west of us, this rail line gets you to O'Hare airport in less than an hour, or downtown in about 10 minutes (it's a bit longer walk to the Blue Line than to the Pink Line) . -#157 Bus (Streeterville): This super convenient bus 1 block south of us on Taylor Street runs during the daytime only and takes you to the Magnificent Mile for upscale shopping on North Michigan Avenue in 25 minutes. -#12 Bus (Roosevelt): This is about 3-4 blocks south of us, runs east-west, and takes you to the Soldier Field stadium and the Roosevelt Road shopping area with Whole Foods, Nordstrom Rack, Best Buy, Core Power Yoga, and much more. Bicycle: You bike? We bike. There is a DIVVY bike share station a block east in Arrigo Park. Get at DIVVY bike-share 24-hour pass with unlimited half-hour rides. Switch out bikes for longer distances. If you have your own bike, you can park it safely on the ground floor of your coach house apartment. It takes 15 to 20 minutes to bike to most downtown locations. Car: Our home is 3 blocks south of I-290 (the Eisenhower), and near I-55 (the Stevenson), I-90 and I-94 (the Dan Ryan and Kennedy). Parking: We provide parking passes for free zoned street parking available on a small shelf as you enter the Coach House along with instructions. Please be very careful about filling out the pass, as City workers seem motivated to issue tickets if the pass is not filled out correctly. We travel a lot and know what it's like to be away from home. That's why we've furnished the apartment with appealing furniture, comfortable beds, plenty of towels (and more towels), soaps, shampoos, and a kitchen outfitted with all the basics plus a few more: Kitchen Aid food processor, toaster, microwave, baking and cooking tools, Calphalon pots & pans. Please note there is no dishwasher. Enjoy complimentary Nespresso coffee, Bigelow teas, bottle water, and snacks. Three blocks to the Medical District. Walk the tree-lined streets of the Little Italy to restaurants of all kinds. Host recommendations include Rosebud for classic Italian, and Asian cuisine on Taylor Street. Stroll in Garibaldi Park steps away, or Arrigo Park a block away.

Dec 11 – 18

ﺩ.ﺇ474 per night
Guest favorite

Guest suite in Chicago

5.0 out of 5 average rating, 290 reviews

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

Apr 1 – 8

ﺩ.ﺇ515 per night
Guest favorite

Apartment in Uptown

4.97 out of 5 average rating, 260 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; small family on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. New!Andersonville, recently voted the coolest neighborhood in US (Timeout’s survey) is only a 15-minute stroll. The CTA's Red Line/Wilson station is 3 blocks away. Overnight street-parking decals also available for guests.

Aug 20 – 27

ﺩ.ﺇ419 per night

Popular amenities for Chicago vacation rentals

Stay near Chicago's top sights

Millennium Park1,243 locals recommend
O'Hare International Airport122 locals recommend
Lincoln Park175 locals recommend
Grant Park332 locals recommend
Shedd Aquarium673 locals recommend
Magnificent Mile597 locals recommend

Chicago fishing vacation rentals

Guest favorite

Apartment in Chicago

4.85 out of 5 average rating, 156 reviews

Your brand new Chicago suite (unit 1F)

Jul 9 – 16

ﺩ.ﺇ335 per night
Guest favorite

Condo in Chicago

4.94 out of 5 average rating, 181 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Sep 25 – Oct 2

ﺩ.ﺇ380 per night
Guest favorite

Home in Chicago

4.89 out of 5 average rating, 332 reviews

Private 3rd Floor Apartment

Dec 17 – 24

ﺩ.ﺇ540 per night
Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 212 reviews

A guest suite centrally located, but so quiet...

Dec 20 – 27

ﺩ.ﺇ382 per night
Guest favorite

Guest suite in Carol Stream

4.94 out of 5 average rating, 279 reviews

Hot Tub, Pool Table, Bar, fishing & Kayak on Lake!

Apr 22 – 29

ﺩ.ﺇ412 per night
Superhost

Apartment in Chicago

4.81 out of 5 average rating, 142 reviews

The Posh Apt. Mins to Downtown & Hyde Park

Apr 18 – 25

ﺩ.ﺇ408 per night
Guest favorite

Townhouse in Chicago

4.98 out of 5 average rating, 224 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

Mar 19 – 26

ﺩ.ﺇ789 per night
Superhost

Condo in Lake View

4.83 out of 5 average rating, 280 reviews

Private studio with free garage parking

Apr 9 – 16

ﺩ.ﺇ550 per night
Guest favorite

Apartment in Chicago

4.83 out of 5 average rating, 388 reviews

Lakeview Charmer -with parking!

Mar 6 – 13

ﺩ.ﺇ635 per night
Guest favorite

Condo in Chicago

4.99 out of 5 average rating, 554 reviews

Urban Comfort in the Heart of Chicago

Jul 22 – 29

ﺩ.ﺇ801 per night
Guest favorite

Condo in Chicago

4.98 out of 5 average rating, 194 reviews

Near Lake Michigan & Wrigley Field

Sep 6 – 13

ﺩ.ﺇ1,046 per night
Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 174 reviews

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

Apr 29 – May 4

ﺩ.ﺇ656 per night

Chicago apartment rentals

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 315 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

Sep 30 – Oct 7

ﺩ.ﺇ488 per night
Guest favorite

Apartment in Chicago

4.87 out of 5 average rating, 481 reviews

Logan Square Studio

Nov 20 – 27

ﺩ.ﺇ376 per night
Guest favorite

Apartment in Chicago

4.97 out of 5 average rating, 116 reviews

Designer Avondale Attic

May 23 – 30

ﺩ.ﺇ393 per night
Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 245 reviews

Andersonville Cozy 1 bedroom basement suite

Sep 17 – 24

ﺩ.ﺇ461 per night
Guest favorite

Apartment in Gold Coast

4.91 out of 5 average rating, 134 reviews

Charming Gold Coast One-Bedroom Near Downtown!

Nov 12 – 19

ﺩ.ﺇ457 per night
Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 122 reviews

Modern Apt with style & comfort in Pilsen Chicago

May 14 – 21

ﺩ.ﺇ515 per night
Guest favorite

Apartment in Chicago

4.87 out of 5 average rating, 268 reviews

1 Bedroom Apartment In Historic Old Town House

Jan 22 – 29

ﺩ.ﺇ535 per night
Guest favorite

Apartment in Chicago

4.93 out of 5 average rating, 198 reviews

Charming Edgewater/Andersonville Garden 1 bdrm.

Mar 16 – 23

ﺩ.ﺇ374 per night
Guest favorite

Apartment in Skokie

4.91 out of 5 average rating, 527 reviews

Cozy Garden Unit in Quiet Neighborhood

Feb 18 – 25

ﺩ.ﺇ469 per night
Guest favorite

Apartment in Humboldt Park

4.98 out of 5 average rating, 102 reviews

Humboldt Park Loft

Sep 4 – 11

ﺩ.ﺇ450 per night
Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 253 reviews

Logan Square 2nd Floor Chicago Victorian

Dec 27 – Jan 3

ﺩ.ﺇ413 per night
Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 180 reviews

Taj Ma-small at Wrigley

Jan 28 – Feb 4

ﺩ.ﺇ449 per night

Chicago homes

Guest favorite

Home in Chicago

4.94 out of 5 average rating, 204 reviews

Modern Home RoscoeVillage/Wrigley Free St Parking

Feb 25 – Mar 4

ﺩ.ﺇ469 per night
Guest favorite

Home in Chicago

4.95 out of 5 average rating, 111 reviews

Cozy & Modern Chic Full House in Trendy Bridgeport

Dec 24 – 31

ﺩ.ﺇ445 per night
Guest favorite

Home in Chicago

4.97 out of 5 average rating, 316 reviews

Cozy garden apartment historic Jackson Bvld.

Dec 20 – 25

ﺩ.ﺇ666 per night
Guest favorite

Home in Berwyn

4.92 out of 5 average rating, 232 reviews

Private apartment with retro vibe

Sep 5 – 12

ﺩ.ﺇ403 per night
Guest favorite

Home in Chicago

4.98 out of 5 average rating, 202 reviews

Wrigleyville Southport Studio

Dec 3 – 10

ﺩ.ﺇ582 per night
Guest favorite

Home in Chicago

4.95 out of 5 average rating, 309 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

Feb 25 – Mar 4

ﺩ.ﺇ521 per night
Guest favorite

Home in Chicago

4.86 out of 5 average rating, 214 reviews

The Avondale Guesthouse

Dec 29 – Jan 5

ﺩ.ﺇ433 per night
Guest favorite

Home in West Town

4.95 out of 5 average rating, 166 reviews

Paradise on the Park

Oct 21 – 28

ﺩ.ﺇ622 per night
Guest favorite

Home in Portage Park

4.98 out of 5 average rating, 175 reviews

The Evergreen House

May 10 – 17

ﺩ.ﺇ498 per night
Guest favorite

Home in Blue Island

4.8 out of 5 average rating, 169 reviews

Warm and comfortable inviting Suburban home !

Jun 19 – 26

ﺩ.ﺇ410 per night
Guest favorite

Home in Chicago

4.96 out of 5 average rating, 195 reviews

Division St Designer Home In Heart of Wicker Park

Jul 18 – 25

ﺩ.ﺇ1,803 per night
Guest favorite

Home in Forest Park

4.9 out of 5 average rating, 218 reviews

Charming dog friendly 2-Bath Bungalow Near Chicago

Jul 25 – Aug 1

ﺩ.ﺇ582 per night

Quick stats about vacation rentals in Chicago

Total rentals

11K properties

Rentals with dedicated workspaces

6.6K properties have a dedicated workspace

Rentals with a pool

1.2K properties have a pool

Pet-friendly rentals

3.3K properties allow pets

Family-friendly rentals

5K properties are a good fit for families

Total number of reviews

476K reviews

Your guide to Chicago

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.


The best time to stay in a vacation rental in Chicago

Chicago’s summers are warm and sunny, which means the rooftops and patios are buzzing, and the days are filled with music and food festivals. This is also when the city's lakeside beaches are at their best, so it’s a popular time for booking Chicago vacation rentals. Fall is chilly but pleasant. Winters are downright cold, and you can expect plenty of snow between the months of December and April, but there’s also plenty of opportunity for ice skating in rinks and snowshoeing and sledding down hills in city parks. There are also wonderful Christmas lights at Navy Pier and throughout the city. Expect relatively cool temperatures and a decent amount of rainfall in spring, and pack your waterproof layers.


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.

Frequently Asked Questions

  • How is the weather in Chicago?

    Chicago experiences a wide range of weather, from hot summers that can reach 95°F (35°C) to chilly winters that can drop to 20°F (-6°C). The city exhibits four distinct seasons, with beautiful spring blossoms, sunny summers, colorful autumns, and snow-dusted winters, perfect for ice skating in Millennium Park.

  • What are some of the best things to do in Chicago?

    In Chicago, you can explore iconic sights like Navy Pier, Cloud Gate in Millennium Park, and Willis Tower's SkyDeck for breathtaking city views. Cultural enthusiasts can immerse themselves in the Art Institute of Chicago or catch an engaging show at the Second City comedy club.

  • What is the best time of year to visit Chicago?

    Summer, from June to August, is often recommended to visit Chicago. During this season, the city hosts various events, including the Chicago Blues Festival and Taste of Chicago, attracting food and music enthusiasts alike. However, the city is vibrant year-round, with winter activities such as ice skating and holiday markets.

  • What are the best places to stay in Chicago?

    Popular areas to stay in Chicago include the vibrant neighborhoods of River North and Gold Coast for their proximity to dining and shopping. Lincoln Park and Lakeview are also often recommended for their leafy streets, local cafes, and proximity to the lake.

  • What are the best places to visit in Chicago?

    Popular places to visit in Chicago include the culturally rich neighborhoods like Chinatown, Little Italy, and Pilsen. Navy Pier, the Magnificent Mile shopping district, as well as green spaces like Grant Park and Lincoln Park, are also frequently suggested.

  • What are some hiking trails in Chicago?

    While Chicago is an urban city, it still has some scenic hiking trails. The Chicago Lakefront Trail, a 18-mile (29 km) path along Lake Michigan, and the North Branch Trail System in the Forest Preserves of Cook County are popular among outdoor enthusiasts.

  • What are some family activities to do in Chicago?

    Families often enjoy exploring the Shedd Aquarium, the Field Museum of Natural History, and the interactive exhibits at the Chicago Children's Museum. A boat tour along the Chicago River, highlighting the city's architectural marvels, is another frequently suggested activity for families.

  • What are some of the best day trip ideas in Chicago?

    For day trips from Chicago, consider a visit to the Indiana Dunes National Park for some beach fun and hiking, or explore the charming town of Geneva for a relaxed pace with boutique shopping. Rockford, with its Anderson Japanese Gardens and Burpee Museum of Natural History, is also a viable option.

  • What types of vacation rentals are available in Chicago?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Chicago. From over 1,180 condo rentals, over 6,030 apartment rentals to over 1,850 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Chicago?

    Yes! Work meets play with ease at over 6,650 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.

Destinations to explore

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