Chicago vacation rentals

Book unique homes, vacation rentals, and more on Airbnb

Top-rated vacation rentals in Chicago

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Guesthouse in Little Italy

4.99 out of 5 average rating, 786 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.

Jan 18 – 25

G$26,094 GYD per night

Guest favorite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 295 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

Oct 22 – 29

G$29,281 GYD per night

Guest favorite

Apartment in Chicago

4.94 out of 5 average rating, 191 reviews

Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

Jul 14 – 21

G$23,882 GYD per night

Guest favorite

Guest suite in Chicago

4.96 out of 5 average rating, 320 reviews

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

Mar 31 – Apr 7

G$18,666 GYD per night

Guest favorite

Apartment in Avondale

4.97 out of 5 average rating, 118 reviews

Designer Avondale Attic

Soak in the beauty of this professionally designed and newly-renovated minimalistic attic in the heart of Chicago's most hip neighborhoods! Every detail of this home was thought through extensively to provide the perfect experience for our guests. Designer furniture, luxury soaps and amenities, a smart TV, high speed wifi, free laundry on site! A quick walk brings you to amazing coffee shops, trendy restaurants, or hop on the Blue Line train to help you get to any part of the city with ease.

Jul 23 – 30

G$24,757 GYD per night

Guest favorite

Guest suite in Chicago

4.98 out of 5 average rating, 111 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Apr 10 – 17

G$19,320 GYD per night

Guest favorite

Apartment in Chicago

4.98 out of 5 average rating, 107 reviews

Humboldt Park Loft

Bright and spacious loft style 1 bedroom/1 bathroom apt in the Humboldt Park neighborhood of Chicago. Renovated A-frame large attic space on the second floor of our house. Private apartment with open lay-out plan, full kitchen, and lots of natural light. Close to Logan Square and Wicker Park neighborhoods. Walking distance to Humboldt Park and the 606 trail. Two blocks to Kimball/Homan and North Ave buses. Quiet residential street with free and easy street parking. Smoke and pet free space.

Oct 18 – 25

G$25,573 GYD per night

Guest favorite

Guest suite in Chicago

4.95 out of 5 average rating, 242 reviews

Great location, private entry and patio!

Large 1 bedroom space tastefully decorated and well equipped. Sleeps 4 (5 with available inflatable). Queen bed in BR, full size futon in LR. Spacious enough for 2 to work comfortably. Use of the patio, fire pit and grill. Located in vibrant Lincoln Square. Steps to the Rockwell brown line el station, restaurants, a bagel shop, and yoga/massage studio. A few blocks away are shops, restaurants and a movie theater! Easy street parking with free permits. Ask about winter specials!

Nov 7 – 14

G$20,419 GYD per night

Guest favorite

Apartment in Chicago

4.93 out of 5 average rating, 187 reviews

Taj Ma-small at Wrigley

I think you are just going to love my apartment. The space features wonderful large windows in both rooms and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a four-minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. It's also a walk to all of the 'Boystown' nightlife. There is no parking available with the apartment.

Jan 24 – 31

G$16,940 GYD per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 266 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; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Andersonville (one of Chicago’s coolest neighborhood is a 15-minute stroll. CTA's Red Line/Wilson train station is 3 blocks away. Overnight street-parking decals also available for guests.

Oct 19 – 26

G$23,703 GYD per night

Superhost

Apartment in Chicago

4.89 out of 5 average rating, 105 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

This gem is steps from Hartigan Beach, an eclectic mix of eateries, small theater venues, public transportation and Fine Wines & Spirits. You'll love my place because of the coziness and proximity to a swimming beach, on a friendly tree lined street. Conveniently situated between Loyola and Northwestern Universities. Rent a Divvy bike, call UBER/LYFT, rent a car and explore all that Evanston, Edgewater and Andersonville has to offer!

Oct 24 – 31

G$24,477 GYD per night

Guest favorite

Apartment in Cicero

4.98 out of 5 average rating, 202 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Quiet city side street. Walking distance to dozens of restaurants and stores. Walking distance to Public Transportation including Metra train, CTA Pink line, Direct CTA Bus to Midway Airport. You will be a short 20-minute drive to Downtown Chicago, 15 minutes to United Center or Soldier Field. Perfect for the quick getaway, the night before your flight, or even the long work assignment. Relax on the Patio with a fire pit and grill.

Feb 25 – Mar 4

G$26,051 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chicago vacation rentals

Free parking on premises

Stay near Chicago's top sights

Millennium Park1,243 locals recommend

O'Hare International Airport122 locals recommend

Grant Park332 locals recommend

Lincoln Park175 locals recommend

Shedd Aquarium673 locals recommend

Cloud Gate473 locals recommend

Other great vacation rentals in Chicago

Guest favorite

Home in Chicago

4.89 out of 5 average rating, 332 reviews

Private 3rd Floor Apartment

Jan 8 – 15

G$26,222 GYD per night

Guest favorite

Condo in Chicago

4.93 out of 5 average rating, 187 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Mar 2 – 9

G$20,725 GYD per night

Guest favorite

Guest suite in Carol Stream

4.94 out of 5 average rating, 285 reviews

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

Nov 24 – Dec 1

G$28,274 GYD per night

Guest favorite

Apartment in Edgewater

4.84 out of 5 average rating, 100 reviews

minimal lakefront apartment

Oct 26 – Nov 2

G$31,532 GYD per night

Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 214 reviews

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

Feb 21 – 28

G$31,149 GYD per night

Guest favorite

Apartment in Evanston

4.97 out of 5 average rating, 408 reviews

Charming, Sunny Apartment with Backyard Garden

Feb 18 – 25

G$32,261 GYD per night

Guest favorite

Condo in Chicago

4.99 out of 5 average rating, 563 reviews

Urban Comfort in the Heart of Chicago

Jul 24 – 31

G$45,550 GYD per night

Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 397 reviews

Andersonville Living

Oct 20 – 27

G$31,746 GYD per night

Show all

Vacation rentals with pools in Chicago

Guest favorite

Guest suite in Bartlett

4.96 out of 5 average rating, 186 reviews

Cozy & Spacious Suite in Quiet Neighborhood

Dec 18 – 25

G$22,774 GYD per night

Guest favorite

Apartment in Chicago

4.87 out of 5 average rating, 156 reviews

Stunning Panoramic Chicago Views & Free Parking

Mar 27 – Apr 3

G$82,713 GYD per night

Guest favorite

Apartment in Chicago

4.89 out of 5 average rating, 463 reviews

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

Aug 3 – 10

G$66,340 GYD per night

Guest favorite

Home in Highland Park

4.9 out of 5 average rating, 125 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Mar 13 – 20

G$237,514 GYD per night

Superhost

Apartment in Itasca

4.77 out of 5 average rating, 181 reviews

King Bed at Chicago Northwest + PET Friendly

Oct 7 – 14

G$238,157 GYD per night

Guest favorite

Condo in Evanston

4.91 out of 5 average rating, 102 reviews

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

Dec 2 – 9

G$45,240 GYD per night

Superhost

Apartment in Chicago

4.86 out of 5 average rating, 190 reviews

Spectacular Corner 2BR Penthouse in the Loop | Roo

Jan 24 – 31

G$70,710 GYD per night

Superhost

Apartment in Chicago

4.87 out of 5 average rating, 110 reviews

Level ◆ Two Bedroom Deluxe Corner Suite + Balcony

Jul 26 – Aug 2

G$178,863 GYD per night

Show all

Chicago apartment rentals

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 238 reviews

Roscoe Village One Bed Lux Apartment Near Wrigley

Nov 18 – 25

G$21,831 GYD per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 262 reviews

Turquoise Wonder - Clean, Cozy & Stylish Apt

Nov 6 – 13

G$21,764 GYD per night

Guest favorite

Apartment in Chicago

4.96 out of 5 average rating, 323 reviews

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

Jan 4 – 11

G$27,574 GYD per night

Guest favorite

Apartment in Oak Park

4.85 out of 5 average rating, 531 reviews

Long stays welcome@warm&cute vintage 2BR

Sep 29 – Oct 6

G$21,064 GYD per night

Guest favorite

Apartment in West Town

4.89 out of 5 average rating, 473 reviews

iKlektik House Chicago / Robin

Oct 20 – 27

G$28,656 GYD per night

Guest favorite

Apartment in Chicago

4.97 out of 5 average rating, 251 reviews

Spacious 1BR apartment in a central location

Oct 1 – 8

G$20,896 GYD per night

Guest favorite

Apartment in Chicago

4.92 out of 5 average rating, 492 reviews

2BR Bursting w/ Character in Hip Logan Square!

Apr 8 – 15

G$30,240 GYD per night

Superhost

Apartment in Chicago

4.81 out of 5 average rating, 124 reviews

Tranquil & Airy 1BR Apt in Lincoln Square

May 7 – 14

G$22,908 GYD per night

Show all

Quick stats about vacation rentals in Chicago

Total rentals
10K properties
Rentals with dedicated workspaces
6.6K properties have a dedicated workspace
Rentals with a pool
1.1K properties have a pool
Pet-friendly rentals
3.3K properties allow pets
Family-friendly rentals
4.8K properties are a good fit for families
Total number of reviews
466K 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 5,870 apartment rentals, over 1,830 house rentals to over 1,100 condo 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 6,560 vacation rentals in Chicago featuring dedicated workspaces. Stay connected and productive in your home away from home.

Chicago vacation rentals

Top-rated vacation rentals in Chicago

Vacation rentals for every style

Cottages

Houses

Apartments

Popular amenities for Chicago vacation rentals

Stay near Chicago's top sights

Other great vacation rentals in Chicago

Home in Chicago

Condo in Chicago

Guest suite in Carol Stream

Apartment in Edgewater

Guest suite in Evanston

Apartment in Evanston

Condo in Chicago

Apartment in Chicago

Vacation rentals with pools in Chicago

Guest suite in Bartlett

Apartment in Chicago

Apartment in Chicago

Home in Highland Park

Apartment in Itasca

Condo in Evanston

Apartment in Chicago

Apartment in Chicago

Chicago apartment rentals

Apartment in Chicago

Apartment in Chicago

Apartment in Chicago

Apartment in Oak Park

Apartment in West Town

Apartment in Chicago

Apartment in Chicago

Apartment in Chicago

Quick stats about vacation rentals in Chicago

Total rentals

Rentals with dedicated workspaces

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Your guide to Chicago

All About Chicago

The best time to stay in a vacation rental in Chicago

Top things to do in Chicago

The Art Institute of Chicago

Willis Tower

Millennium Park

Frequently Asked Questions

How is the weather in Chicago?

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

What is the best time of year to visit Chicago?

What are the best places to stay in Chicago?

What are the best places to visit in Chicago?

What are some hiking trails in Chicago?

What are some family activities to do in Chicago?

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

What types of vacation rentals are available in Chicago?

Are there vacation rentals with a dedicated workspace in Chicago?

Destinations to explore