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Chicago vacation rentals

Vacation rentals in Chicago by owner — compare homes, condos and cabins, message verified hosts, and book direct with no service fees.

Chicago draws visitors with attractions like Millennium Park, Navy Pier, the Art Institute of Chicago, and Wrigley Field. The city's vibrant cultural scene includes events such as Lollapalooza, the Chicago Blues Festival, and iconic architecture tours. Houfy connects you directly with local hosts in Chicago, allowing bookings that keep costs low. Explore neighborhood lofts, downtown apartments, and lakeside condos across Lincoln Park, Lakeview, and the Loop. Summer along Lake Michigan is ideal for outdoor festivals and cruising the Chicago River.

Top-Rated Vacation Homes in Chicago

Browse the highest rated vacation properties in Chicago.

Chicago 2Br Condo - Downtown Access

2 bd·1 ba
5· 3

Modern Western Logan Square Flat Healy Metra Stop

2 bd·1 ba
4.75· 24

$767.00 USD total for 3 nights

Sep 22 – 25, 2026

My husband and I had a great visit to Logan Square and the Chicago area while staying at this location. The home was spotless, looked and functioned exactly as described, and had unique architectural features that made staying there a treat. We could walk to the Square, catch a ride with friends, and found parking pretty easy in the surrounding park/residential areas. Catching a ride share downtown is also very simple as the home is located near main arterial roads. We had no problem pre-scheduling a ride share to take us downtown during peak times, and to the airport early in the morning of our departure. The surrounding neighborhood is historic and classic Chicago which we appreciated. We stayed during the July 4 holiday weekend, and recommend visiting during this time for a full "Chicago experience" -- a mix of locals and tourists, with notably less traffic and other congestion compared to other major cities during this holiday weekend.
N. · Stay July 2024

MFL 3 East

4 bd·4 ba
4.99· 93

$3,302.46 USD $2,836.70 USD total for 3 nights

Sep 22 – 25, 2026

Excellent location, excellent stay, excellent service
We were a group of 8 women staying for 5 days at this property in a combination writing retreat/ladies getaway. We had an absolutely fantastic experience in the loft and would 100% recommend it to other groups, as well as stay again. The communication with Carole was top notch, including her meeting several requests that we had, as well as offering recommendations. We had everything we needed for the 5 days and were so happy throughout our entire stay. The location is top notch and just about anything you want is within a few blocks walk, from restaurants to Whole Foods to Target to a liquor store to casual shopping , entertainment and more. You can't ask for a better location! In addition, the loft is well insulated and the *only* outside noise that ever came to us was from fire engines going by. Otherwise, the loft was quiet and well-contained. With 4 bathrooms and 4 bedrooms, as well as a variety of beds/sleeping options, there's plenty of room for a large group. Possibly our only request would have been an additional sofa or longer sofas, as we did spend a lot of time at the loft and would have liked more lounging options/comfortable seating options (the dining room chairs are great for dining but not long-term seating/working). The kitchen was fully stocked with everything we needed in terms of utensils, pots, pans, etc for cooking, and there wer even a few random spices. One touch we absolutely loved was the bags of ice provided in the freezer. That's something I wouldn't have though tto ask for but would now love to see in every vacation rental we stay in. There was also some coffee, tea and sugar provided--a top notch service all the way! In short, this is a fantastic choice for your next vacation stay as a group, I can't recommend it highly enough, and I hope we get to experience Carole and Basil's hospitality again some day!
A. W. · Stay September 2019

Artistic Stay near Hyde Park: 2 Living, Courtyard

3 bd· ba
5· 92

$924.00 USD total for 3 nights

Oct 4 – 7, 2026

We loved our stay at this exquisite & perfectly curated home. Perfect location, within walking distance to the school, supermkts & public transportation. We were definitely blown away & mesmerized as we walked into each area and room in the home. We even took notes for our own future home decorations. The artwork is representative of Black history, which goes perfectly with the home’s location of South Chicago. While at the same time, walking through the home takes you on an int’l trip. It has a very homey feel; the Teens loved it, especially playing Michael Jackson from the fridge while we all took in the decor. The feedback that we would give is to please provide add’l blankets for the bedding & to please run the gas heater a day before to avoid the weird smell that may come out of it, if it has not been turned on for a while. Elisabeth & Juaquan were very attentive and Juaquan came right over when we informed him of the funny smell. We will definitely stay again, LONGER. Thank you!?
V. · Stay November 2025

Large Cozy 3BR near UChicago Medical Midway Museum

3 bd·1 ba
5· 8
We had a great stay at Kenneth's! Lot of space, cozy and clean home, all amenities as described, great communication and easy on-street parking on the south side. Ken was a great host: very proactive, friendly, helpful, and had good communication regarding any questions we had during the stay. He was kind enough to accommodate our requests which made our trip (with 2 seniors) much less troublesome. Would gladly recommend his Airbnb.
B. · Stay September 2024

Chicago Lakefront · Fire Pit Patio · Beach Across

1 bd·1 ba
5· 1

$447.00 USD $357.60 USD total for 3 nights

Sep 22 – 25, 2026

The apartment was perfect for our stay in Chicago. It was just a couple blocks from the train station, perfect for getting to Guaranteed Rate Field. Right across the street is the beach and there are plenty of stores and restaurants nearby. The hosts were great at communicating if we needed anything and very nice! The apartment was nice and clean! If you want the best of the city and Lake Michigan for a great price, stay here!
L. · Stay May 2026

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Vacation houses with pools in Chicago

Cool off in style with these amazing pool homes in Chicago.

Charming Garden Retreat

5 bd· ba

Pet friendly vacation rentals in Chicago

Bring your furry friend along! Browse pet-welcoming homes in Chicago.

Why visit Chicago

Discover what makes Chicago a perfect vacation rental destination.

Theatre & Comedy Scene

World-renowned for vibrant performances.

Catch a show at the iconic Chicago Theatre or laugh the night away at The Second City, both located within a mile of downtown.

Magnificent Mile

Shop iconic brands on Michigan Avenue.

This famous stretch is home to over 460 retailers including high-end boutiques and flagship stores, just a 10-minute walk from Millennium Park.

Deep-Dish Delicacies

Savor Chicago's pizza heritage.

Try a pie at Lou Malnati's or Giordano's, staples for deep-dish enthusiasts, both easy to access from the Loop.

Art Institute of Chicago

Home to thousands of artworks.

Located in Grant Park, this museum features pieces from Impressionist masters. It’s just a short walk from the city center.

Where to stay in Chicago

The best areas and neighborhoods for your vacation rental in Chicago.

The Loop

Home to Chicago's iconic architecture and business district, with a lively arts scene and green spaces like Millennium Park.

Best for: business travelers, architecture enthusiasts, first-time visitors

Wicker Park

Known for vibrant street art and eclectic music venues, a haven for creative spirits and foodies, offering unique dining and shopping.

Best for: young travelers, musicians, artists

Lincoln Park

Features a large green space hosting the free-admission Lincoln Park Zoo, along with various cultural institutions and family-friendly activities.

Best for: families, outdoor lovers, zoo enthusiasts

Hyde Park

A cultural hub with the University of Chicago and the Museum of Science and Industry, rich in history and academic prestige.

Best for: history buffs, academics, museum-goers

Find Chicago vacation rentals that suit your style

Apartments, vacation homes, condos and more — pick the kind of Chicago vacation rental you want, then book it direct with the host.

Chicago vacation rentals with free WiFi, hot tub or air conditioning

Free WiFi, hot tub, air conditioning and more — every Chicago vacation rental here is listed by a verified host and bookable direct, with the price the host set.

Top attractions in Chicago

All within driving distance of Chicago vacation rentals.

The Art Institute of Chicago

Houses over 300,000 artworks, from ancient to modern. · 0.5 miles

Lincoln Park Zoo

Free-entry zoo with diverse animal exhibits and conservation programs. · 3 miles

Chicago Symphony Orchestra

World-class performances in a renowned venue. · 0.4 miles

Magnificent Mile

Premier shopping district with hundreds of stores. · 1 mile

Millennium Park

Famous for Cloud Gate, it's a center for music and art. · 0.2 miles

The Field Museum

Natural history museum featuring the famous T. rex, Sue. · 1.2 miles

Best Time to Visit Chicago

Best months to visit are May, June, and September with mild temperatures (60s-70s °F) and comfortable weather.

For lower prices and fewer crowds, November to March is the best time to book.

Best valueNov – Mar

SepNow

75°F24°C

Rainfall Moderate

Demand Mid

Oct

63°F17°C

Rainfall Moderate

Demand Mid

Nov

48°F9°C

Rainfall Moderate

Demand Low

Dec

36°F2°C

Rainfall Moderate

Demand Low

Jan

31°F-1°C

Rainfall Moderate

Demand Low

Feb

36°F2°C

Rainfall Moderate

Demand Low

Mar

47°F8°C

Rainfall Moderate

Demand Low

Apr

59°F15°C

Rainfall Moderate

Demand Mid

May

70°F21°C

Rainfall Moderate

Demand Mid

Jun

79°F26°C

Rainfall Moderate

Demand Peak

Jul

84°F29°C

Rainfall Moderate

Demand Peak

Aug

82°F28°C

Rainfall Moderate

Demand Peak

Getting to and around Chicago

Chicago offers extensive public transit, major airports, and bike-friendly streets for easy navigation.

Airports
O'HARE INTERNATIONAL AIRPORT
Located 17 miles northwest of downtown, offering global connections.
MIDWAY INTERNATIONAL AIRPORT
Located 10 miles southwest of downtown, convenient for domestic flights.
Public Transit
CHICAGO 'L' TRAINS
Run by the CTA, providing access across the city and suburbs.
CTA BUS SERVICE
Extensive network serving all major neighborhoods and attractions.
Biking
DIVVY BIKE SHARE
Available citywide with numerous stations, convenient for short trips.

Similar vacation rentals near Chicago

Homes within 60 miles of Chicago, from verified hosts.

Hot Tub in the Woods | Winter Getaway Cozy Retreat

3 bd·2 ba
4.87· 138

$2,111.52 USD total for 3 nights

Sep 22 – 25, 2026

Stunning Lake house on peaceful Sta

5 bd· ba
4.86· 22

$3,582.32 USD total for 5 nights

Oct 12 – 17, 2026

*King bed *Outdoor Living *Sought-After Area

3 bd· ba
5· 130

$1,418.00 USD total for 3 nights

Sep 27 – 30, 2026

Cute 2 br with King and Queen

2 bd·1 ba
4.95· 20

Single-Family Home. Fully Furnished

3 bd·2 ba
5· 16

$1,935.00 USD total for 6 nights

Sep 22 – 28, 2026

Lovely 1 bed room apartment, all to yourself.

1 bd·1 ba
4.87· 94

$406.60 USD total for 3 nights

Sep 27 – 30, 2026

Waterfront Cottage/sauna/kayaks/firepit/dock

1 bd·1 ba
4.88· 40

Modern forest retreat: fast wifi, hot tub, firepit

4 bd·3 ba
5· 27

$2,295.00 USD total for 3 nights

Sep 22 – 25, 2026

Walk to Downtown! 6-Bedroom Home

6 bd·3 ba

$1,084.00 USD total for 3 nights

Sep 22 – 25, 2026

$1,214.00 USD total for 3 nights

Sep 28 – Oct 1, 2026

Explore near Chicago

Cities and towns within driving distance of Chicago, each bookable direct with the host.

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Quick answers about booking vacation rentals in Chicago and what direct booking on Houfy actually means.

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