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2026-11-09
2026-11-10
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Vacation Rentals in Chicago

Vibrant 1Br Apartment In Roscoe Village - Marshfield N3

3429 North Marshfield Avenue, Chicago, United States Show map

The 1-bedroom Vibrant 1Br Apartment In Roscoe Village - Marshfield N3 Chicago lies around 800 metres from Saint Alphonsus Catholic Church and around 5 minutes on foot from Paulina tube station. The… More

From US$ 266 Book Now

Warm & Inviting 2Br Apartment - Fullerton 1B

4458 North Kedzie Avenue, Chicago, United States Show map

The 102 m² Warm & Inviting 2Br Apartment - Fullerton 1B Chicago lies merely 1.7 km from Horner Park and approximately a 5-minute walk from Kedzie tube station. More

From US$ 372 Book Now

Townhome

5434 North Kenmore Avenue, Chicago, United States Show map

Townhome Chicago offers easy entry to such city sights as Saint Ita's Roman Catholic Church, situated nearly a 5-minute walk away. More

From US$ 81 Book Now

Walk To Lake Michigan: Chicago Apt W/ Yard

3975 S Ellis Ave, Chicago, United States Show map

The spacious 121 m² Walk To Lake Michigan: Chicago Apt W/ Yard is located within an 8-km distance of Chicago Union train station and about 5 minutes on foot from Mandrake Park. The maximum occupancy… More

From US$ 246 Book Now

Mccormick Place Luxurious And Spacious 3Br In Downtown Chicago With Optional Parking Sleeps 10 Guests

2036 South Michigan Avenue 601, Chicago, United States Show map

Featuring a prime location only a 5-minute walk from Second Presbyterian Church of Chicago, the 200 m² Mccormick Place Downtown: Luxurious 3BR/2BA for 10 Chicago apartment accommodates up to 10… More

From US$ 550 Book Now

Close To Downtown And Comfortable - Free Parking

918 W 53Rd St, Chicago, United States Show map

The 4-room Close To Downtown And Comfortable - Free Parking Chicago apartment offers easy entry to such city sights as The Chicago-Salem Church, situated nearly a 5-minute walk away. More

From US$ 132 Book Now

Apartment Sleeps 4 With Free Parking

5728 West Higgins Avenue, Chicago, United States Show map

Located a 25-minute walk from the historic Noble-Seymour-Crippen House, the spacious Apartment Sleeps 4 With Free Parking Chicago overlooks the garden. This apartment offers a private parking lot on… More

From US$ 197 Book Now

Gorgeous 5 Bedroom Gem With Games

7928 South Ada Street, Chicago, United States Show map

Up to 16 guests can stay at the 5-bedroom Gorgeous 5 Bedroom Gem With Games Chicago villa and enjoy Saint Sabina Roman Catholic Church, located a mere 6 minutes' walk away. This property features… More

From US$ 2793 Book Now

The Karlov. Gorgeous ,Spacious 2Bd/ 1Ba W/ Parking

4109 West Pierce Avenue, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 2-bedroom The Karlov. Gorgeous ,Spacious 2Bd/ 1Ba W/ Parking Chicago apartment, which is within a 7-km distance of Frank Lloyd Wright Home and Studio… More

From US$ 537 Book Now

South Loop Rooftop With In & Out Parking 1

633 South Lasalle Street, Chicago, United States Show map

South Loop Rooftop With In & Out Parking 1 Chicago apartment is nestled in Downtown Chicago, which is an incredible destination to experience, a 6-minute walk from the restaurant Villains Chicago. 6… More

From US$ 854 Book Now

Stylish Chicago Retreat: Walk To Loyola University

6242 N Kenmore Ave Unit D, Chicago, United States Show map

The 4-bedroom Stylish Chicago Retreat: Walk To Loyola University villa offers swift access to various city sites, such as Mundelein College, situated nearly a 5-minute walk away. Providing guests… More

From US$ 687 Book Now

Modern Apt W Private Entrance Washer Dryer Free Parking

2947 West Fargo Avenue, Chicago, United States Show map

The 46 m² Modern Apt W Private Entrance Washer Dryer Free Parking Chicago features a convenient location around 5 minutes' walk from Sephardic Congregation Orthodox Synagogue and hosts up to 6 guests… More

From US$ 274 Book Now

5Br 5Ba Architectural Estate-Theatre Gym Rooftop

1856 North Fairfield Avenue, Chicago, United States Show map

Located in Logan Square with plenty of bars and restaurants at an affordable price, just a 5-minute walk from Katherine Anne Confections, 5Br 5Ba Architectural Estate-Theatre Gym Rooftop Chicago… More

Book Now

Super Amazing Place To Stay Near Downtown! Free Parking

918 West 53Rd Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 3-room Super Amazing Place To Stay Near Downtown! Free Parking Chicago apartment, which is within 7 km of the premier natural-history Field Museum and… More

From US$ 99 Book Now

Urbaneden Loft Apartment

3523 West Chicago Avenue, Chicago, United States Show map

Set approximately a 25-minute walk from Humboldt Public Park, the 2-bedroom Urbaneden Loft Apartment Chicago comprises a patio and a balcony overlooking the garden. At the spacious 102 m² apartment… More

From US$ 150 Book Now

5 Bedroom Huge House In Best Location Parking Fireplace Back Yard

1426 North North Park Avenue, Chicago, United States Show map

Nestled about a 25-minute walk from the skyscraper 360 Chicago Observation Deck, 5 Bedroom Huge House In Best Location Parking Fireplace Back Yard Chicago villa is boasting a sunbathing terrace and a… More

From US$ 754 Book Now

Cozy 2Br South Loop Condo With Optional Parking And Gym Near Mccormick Place, Public Transit & City Hotspots

2036 South Michigan Avenue 706, Chicago, United States Show map

The spacious 2-bedroom Cozy 2Br South Loop Condo With Optional Parking And Gym Near Mccormick Place, Public Transit & City Hotspots Chicago is located 3.6 km from Chicago Union train station and… More

From US$ 375 Book Now

Club Salon Sleeps 10-20 Free Parking & Tv

3152 North Pine Grove Avenue, Chicago, United States Show map

A mere 0.9 km from Belmont underground station, the 3-bedroom Club Salon Sleeps 10-20 Free Parking & Tv Apartment Chicago is nestled in a beach area of Chicago, about a 5-minute walk from Laugh… More

From US$ 1222 Book Now

Convenient 2Br Suite In Prime Location With Gym Access & Optional Parking Near Mccormick Place And Soldier Field

2036 South Michigan Avenue 605, Chicago, United States Show map

The spacious 80 m² Convenient 2Br Suite In Prime Location With Gym Access & Optional Parking Near Mccormick Place And Soldier Field Chicago is located nearly 5 minutes on foot from the indoor… More

From US$ 463 Book Now

Stone Mansion Sleeps 10-20 Free Tv & Parking

3152 North Pine Grove Avenue, Chicago, United States Show map

Located in Lakeview, which is one of the 77 community areas of Chicago, Illinois, the 4-bedroom Stone Mansion Sleeps 10-20 Free Tv & Parking Apartment Chicago is a mere 7 minutes' walk from Belmont… More

From US$ 1222 Book Now

Charming Chicago Apt

2207 West 18Th Street, Chicago, United States Show map

The spacious 2-bedroom Charming Chicago Apt lies approximately 6 km from the 5 million US gal Shedd Aquarium and about 5 minutes' walk from Western tube station. The apartment is situated 3.9 km from… More

From US$ 342 Book Now

Roscoe Village Family Hideaway

1811 West Eddy Street, Chicago, United States Show map

Up to 14 guests can stay at the 4-bedroom Roscoe Village Family Hideaway Chicago villa and enjoy Juniper Playlot Park, located nearly a 5-minute walk away. Located just 1.4 km from the baseball… More

From US$ 790 Book Now

Fully Furnished Bedroom Near Medical District And Uic

2820 West Arthington Street, Chicago, United States Show map

Fully Furnished Bedroom Near Medical District And Uic Chicago apartment is located 7 km from the premier natural-history Field Museum and 25 minutes' walk from the modern United Center Arena. More

From US$ 83 Book Now

Medical District 2Br With Jacuzzi & Parking

2329 West Harrison Street Unit 1, Chicago, United States Show map

The spacious 111 m² Medical District 2Br With Jacuzzi & Parking Apartment Chicago is a good choice for accommodating up to 4 guests, offering a prime setting within a 6-km distance of the Oak… More

From US$ 216 Book Now

Beautiful Chicago 2Bd 1Ba

4107 West Pierce Avenue, Chicago, United States Show map

The 2-bedroom Beautiful Chicago 2Bd 1Ba Apartment features a convenient location 2.7 km from the 184-acre Garfield Park Conservatory and hosts up to 4 guests. At this spacious apartment, Wi-Fi and… More

From US$ 882 Book Now

Afrique Francaise De Woodlawn 2

6554 South Rhodes Avenue 2, Chicago, United States Show map

The spacious Afrique Francaise De Woodlawn 2 Apartment Chicago lies in a convenient location in Chicago, within 200 metres of Vernon Baptist Church. Wi-Fi and private car parking are among the… More

From US$ 85 Book Now

Mccormick Oasis With Balcony, Optional Parking, Patio And Gym Sleeps 6 Near Mccormick Place, Grant Park, Soldier Field & Museum Campus

61 East 21St Street Apartment 621, Chicago, United States Show map

Located merely 250 metres from Cermak-McCormick Place underground station, the spacious 84 m² Mccormick Oasis With Balcony, Optional Parking, Patio And Gym Sleeps 6 Near Mccormick Place, Grant Park… More

From US$ 417 Book Now

Brilliant Downtown Chicago 3-Bedroom Condominium

158 West Huron Street 3C, Chicago, United States Show map

Located in Downtown Chicago, which is an amazing shopping destination lined with stores, boutiques, galleries and retail centers, a 5-minute walk from the basement Spybar Dance Club, the spacious… More

From US$ 418 Book Now

River North Rooftop With In And Out Parking 1

153 West Ohio Street, Chicago, United States Show map

The spacious 95 m² River North Rooftop With In And Out Parking 1 Chicago apartment is a good choice for accommodating up to 6 guests, offering a prime setting within 25 minutes' walk of the large… More

From US$ 552 Book Now

Parisian Retreat 6Min To Main Quandrangle U Of C

6502 South Maryland Avenue 1, Chicago, United States Show map

Parisian Retreat 6Min To Main Quandrangle U Of C Apartment Chicago is located a mere 1.8 km from the private research University of Chicago and 25 minutes on foot from the leading research center… More

From US$ 1026 Book Now

Cosy Room Near Medical District With Private Balcony

2820 West Arthington Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at Cosy Room Near Medical District With Private Balcony Chicago, which is 7 km from the Oak Magnificent Mile Street and 15 minutes' drive from the - art Shedd… More

From US$ 49 Book Now

Boutique Garden House Chicago 3-Story Sleeps 12

7131 South Michigan Avenue, Chicago, United States Show map

Up to 12 guests can stay at the 5-bedroom Boutique Garden House Chicago 3-Story Sleeps 12 Villa and enjoy First Progressive Church of Christ, located approximately 5 minutes' walk away. Located 4.3… More

From US$ 629 Book Now

2Br Designer Loft Modern Luxe In City Center

160 North Elizabeth Street, Chicago, United States Show map

Nestled a mere 5 minutes' walk from City Winery, the spacious 2Br Designer Loft Modern Luxe In City Center Chicago apartment offers quick access to numerous tourist attractions nearby. This apartment… More

From US$ 507 Book Now

Spacious South Loop 2Br Apartment Near Mccormick Place, Soldier Field & Downtown Chicago

2036 South Michigan Avenue Unit 603, Chicago, United States Show map

The 2-bedroom Spacious South Loop 2Br Apartment Near Mccormick Place, Soldier Field & Downtown Chicago is located in South Loop, set including historic Printers Row, and Cermak-McCormick Place tube… More

From US$ 836 Book Now

Gorgeous North Kenwood Hyde Park Unit

4326 South Greenwood Avenue, Chicago, United States Show map

Situated only an 8-minute stroll from Muddy Waters' House, the 3-bedroom Gorgeous North Kenwood Hyde Park Unit Apartment Chicago also boasts easy access to Chicago Union train station which is… More

From US$ 337 Book Now

Spacious Room By Medical District & Uic

2820 West Arthington Street, Chicago, United States Show map

Situated within a 7-km distance of The Art Institute of Chicago, Spacious Room By Medical District & Uic Chicago also boasts easy access to Chicago Union train station which is approximately a 10… More

From US$ 56 Book Now

Flexhome Wicker Park - Stylish 2Br - Sleeps 6

2149 W Division St, Chicago, Il 60622, Usa, Chicago, United States Show map

Featuring a convenient location within 5 minutes' walk of Holy Trinity Orthodox Cathedral, the spacious 102 m² Flexhome Wicker Park - Stylish 2Br - Sleeps 6 Chicago apartment accommodates up to 6… More

From US$ 629 Book Now

Close To Downtown - Free Parking

944 West 52Nd Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 4-room Close To Downtown - Free Parking Chicago apartment, which is 17 minutes' stroll from House of Prayer for All People and within 6 km of the… More

From US$ 34 Book Now

Chic Cozy 3Br Michigan Avenue Spacious Suite Close To Iconic Chicago Landmarks & Attractions

2036 South Michigan Avenue 609, Chicago, United States Show map

The 100 m² Chic Cozy 3Br Michigan Avenue Spacious Suite Close To Iconic Chicago Landmarks & Attractions offers easy access to such tourist sites as Second Presbyterian Church of Chicago, located… More

From US$ 500 Book Now

New! Spacious Art Deco Modern 5 Bd/3Ba Condo

1465 West Thomas Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 5-bedroom New! Spacious Art Deco Modern 5 Bd/3Ba Condo Chicago, which is within 6 km of the - art Shedd Indoor Aquarium and about a 10-minute ride from… More

From US$ 708 Book Now

Sunny, Spacious, 3Br 1Ba Davlin Inn Chicago

3068 North Davlin Court, Chicago, United States Show map

Featuring a convenient location, the 121 m² Sunny, Spacious, 3Br 1Ba Davlin Inn Chicago offers views of the garden, and is about a 20-minute walk from Uncharted Books. The apartment is situated… More

From US$ 719 Book Now

South Loop 3 Bedroom Apt

1314 South Wabash Avenue, Chicago, United States Show map

Situated only 1.4 km from the lakefront park "Museum Campus", the spacious 112 m² South Loop 3 Bedroom Apt Chicago also boasts easy access to Chicago Union train station which is nearly a 15-minute… More

Book Now

Urban Coach Penthouse - Near Train, Medical District, And Downtown

2846 West 21St Street Coach 2, Chicago, United States Show map

The spacious Urban Coach Penthouse - Near Train, Medical District, And Downtown Apartment Chicago is located a 5-minute walk from Our Lady of Tepeyac Parish and overlooks the city. This apartment can… More

From US$ 101 Book Now

Tiny House - Chicago Pilsen Neighborhood

2325 South Hoyne Avenue, Chicago, United States Show map

The 46 m² Tiny House - Chicago Pilsen Neighborhood Apartment offers proximity to such tourist attractions as Saint Paul Roman Catholic Church, situated approximately 5 minutes' walk away. 4.8 km from… More

From US$ 135 Book Now

Mccormick Place Spacious 5Br Suite With Pool Table & Optional Parking Sleeps 10 Near Soldier Field And Grant Park

2010 South Wabash Avenue 3F, Chicago, United States Show map

Mccormick Place Spacious 5Br Suite With Pool Table & Optional Parking Sleeps 10 Near Soldier Field And Grant Park Chicago is located 2.2 km from Chicago Union train station and approximately a 5… More

From US$ 770 Book Now

Charming 3Br Escape In The Heart Of Hyde Park

5229 S Drexel Ave, Chicago, United States Show map

Located around 10 km from Chicago Union railway station, Charming 3Br Escape In The Heart Of Hyde Park Apartment Chicago is a mere 9 minutes' walk from Smart Museum of Art. More

From US$ 1150 Book Now

1Br Tranquil & Airy Apartment In Lincoln Square - Campbell Rep

4603 North Campbell Avenue, Chicago, United States Show map

Located approximately a 25-minute walk from Andersonville, the 65 m² 1Br Tranquil & Airy Apartment In Lincoln Square - Campbell Rep Chicago is around 7 km from a top family-friendly place like the 35… More

From US$ 256 Book Now

Trendy Studio Apartment In Chicago - Kenwood 103 & 303 Rep

5532 South Kenwood Avenue, Chicago, United States Show map

Trendy Studio Apartment In Chicago - Kenwood 103 & 303 Rep is located around a 5-minute walk from Hyde Park Union Church and 2.9 km from Lakefront Trail. More

From US$ 143 Book Now

1Br Stylish & Modern Chicago Apartment - Kenwood 508 Rep

5220 South Kenwood Avenue, Chicago, United States Show map

The 1-bedroom 1Br Stylish & Modern Chicago Apartment - Kenwood 508 Rep is located approximately 10 km from Chicago Union train station and about 5 minutes' walk from Hyde Park Records. More

From US$ 235 Book Now

2Br Enticing Apt In Chicago Near Restaurants - Belmont A2 A4 Rep

1623 West Belmont Avenue, Chicago, United States Show map

The 800 m² 2Br Enticing Apt In Chicago Near Restaurants - Belmont A2 A4 Rep is located 2.2 km from the baseball stadium "Wrigley Field" and merely an 11-minute walk from Southport Lanes Bowling Alley. More

From US$ 531 Book Now