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

Modern Historic Loft 19Ft Ceilings, Gym, Heated Parking, Skyline Views, Balcony

1524 South Sangamon Street 709, Chicago, United States Show map

Featuring a convenient location right around the corner from 16th Street Murals, the spacious 112 m² Modern Historic Loft 19Ft Ceilings, Gym, Heated Parking, Skyline Views, Balcony Apartment Chicago… More

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West Town Estate 6Br, Game Room, Decks, 5Gbps

851 N Fairfield Ave, Chicago, United States Show map

Located merely 6 minutes' walk from Komoda Gift Shop, the 6-bedroom West Town Estate 6Br, Game Room, Decks, 5Gbps Chicago villa gives easy access to various tourist attractions in the area. The… More

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2 Mi To Rainbow Beach Park: South Side Charmer!

8320 S Burnham Ave, Chicago, United States Show map

The 150 m² 2 Mi To Rainbow Beach Park: South Side Charmer! Chicago apartment is located about 6 km from the Sprawling hands-on Museum of Science and Industry and only a 5-minute walk from House Of… More

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2Br Near Obama Presidential Ctr And Uofc Med Ctr

6135 South Drexel Avenue 3B, Chicago, United States Show map

The 111 m² 2Br Near Obama Presidential Ctr And Uofc Med Ctr Apartment Chicago offers proximity to such tourist attractions as Lorado Taft's Midway Studios, situated around 5 minutes' walk away. The… More

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W Loop 1Br W Gym Pool Nr Fulton Mkt Chi-289

939 W Washington Blvd, Chicago, Il 60607, Usa, Chicago, United States Show map

Situated nearly 5 minutes' walk from Kavi Gupta Gallery, the 1-bedroom W Loop 1Br W Gym Pool Nr Fulton Mkt Chi-289 Apartment Chicago can host up to 2 guests in Chicago. This 58 m² apartment offers… More

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Sleeps 18 • 8Br • Game Room • Gym • Theater

4038 N Central Ave, Chicago, Il 60634, Usa, Chicago, United States Show map

The 8-bedroom Sleeps 18 • 8Br • Game Room • Gym • Theater Chicago villa is located approximately 5 minutes' walk from Romanian Eastern Orthodox Church of Saint Mary and allows guests to enjoy ping… More

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Blueground The Loop Pool Gym Nr Park Chi-1187

North Garland Court 201, Chicago, United States Show map

Featuring a prime location nearly 5 minutes' walk from Chicago-style pizza, the spacious 1-bedroom Blueground The Loop Pool Gym Nr Park Chi-1187 Apartment Chicago accommodates up to 2 guests. This 80… More

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Bridgestreet At The Sterling

345 North Lasalle Blvd., Chicago, United States Show map

Located in Streeterville with a continual thrum of cabs and buses connecting people to other parts of the city, the 50-storey Bridgestreet At The Sterling Chicago apartment is around 5 minutes' walk… More

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Lincoln Park Studio W Wd Lounge Nr L Chi-608

1515 N Fremont St, Chicago, Il 60642, Usa, Chicago, United States Show map

Located in Near North Side, which is home to iconic skyscrapers like the 1920s Wrigley Building, as well as 360 Chicago, a 94th-floor observation deck 25 minutes' walk from Fourth Presbyterian Church… More

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The Reset Space A Minimalist 1Br Oasis

610 East 74Th Street Unit 1B, Chicago, United States Show map

Situated about a 5-minute walk from Park Manor Christian Church, the 1-bedroom The Reset Space A Minimalist 1Br Oasis Chicago apartment offers guests easy access to various tourist attractions nearby… More

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River N 1Br W Gym Pool Wd Nr L Chi-124

8 E Huron St, Chicago, Il 60611, Usa, Chicago, United States Show map

Located 0.7 km from the skyscraper 360 Chicago Observation Deck, River N 1Br W Gym Pool Wd Nr L Chi-124 Chicago apartment accommodates up to 2 guests. Wi-Fi is provided for both business and leisure… More

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Sleep 14 Downtown, Vintage 5Bd-2Ba Gym & Patio

731 South Plymouth Court 801+802, Chicago, United States Show map

Located in Printer's Row with roots dating back to the 1880s as the printing hub of America's Midwest, the 5-bedroom Sleep 14 Downtown, Vintage 5Bd-2Ba Gym & Patio Apartment Chicago is a mere 7… More

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Hancock Lookout|Steps To Beach&Transit, Chi Views

1701, 1220 North State Parkway, Chicago, United States Show map

Situated merely 11 minutes' walk from the skyscraper 360 Chicago Observation Deck, the 2-bedroom Hancock Lookout|Steps To Beach&Transit, Chi Views Chicago villa provides access to numerous tourist… More

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Chicago Skyline 2Br - 6 Min To Millennium Park

8 East 9Th Street, Chicago, United States Show map

Chicago Skyline 2Br - 6 Min To Millennium Park Apartment lies only 1.5 km from Macy's on State Street and within 5 minutes' drive of Roosevelt tube station. The spacious apartment is situated only 1. More

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Blueground River North Doorman Pool Gym Chi-1094

505 North State Street, Chicago, Il, Usa, Chicago, United States Show map

Located only a 5-minute walk from Chicago-style pizza and the scenic Chicago Riverwalk Walkway, Blueground River North Doorman Pool Gym Chi-1094 Chicago apartment features views of the city. At the… More

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River North 1Br W Gym Lounge Roof Nr L Chi-838

8 E Huron St, Chicago, Il 60611, Usa, Chicago, United States Show map

Located just 9 minutes' stroll from the downtown Museum Of Contemporary Art Chicago, the spacious 63 m² River North 1Br W Gym Lounge Roof Nr L Chi-838 Chicago apartment accommodates up to 2 guests. More

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Downtown 3Bd Near Park Museums #7

829 South Wabash Avenue #1307, Chicago, United States Show map

Featuring a prime location only 6 minutes' walk from the American Museum of Contemporary Photography, the spacious 3-bedroom Downtown 3Bd Near Park Museums #7 Apartment Chicago accommodates up to 6… More

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Historic 1930S Retreat! Walk To Wicker Park

2021 W Dickens Ave, Chicago, United States Show map

Offering access to entertainment venues such as the live music venue "Congress Theater", situated only 1.3 km away, the 2-bedroom Historic 1930S Retreat! Walk To Wicker Park Villa Chicago can host up… More

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South Loop 2Br W Rooftop 3 Blocks To Grant Park Chi-1018

1401 S State St, Chicago, Il 60605, Usa, Chicago, United States Show map

Overlooking the city, the spacious 2-bedroom South Loop 2Br W Rooftop 3 Blocks To Grant Park Chi-1018 Chicago apartment is nearly 20 minutes' walk from the lakefront park "Museum Campus" in Chicago. More

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Bridgeport Bungalow Sleeps 4

447 West 27Th Street, Chicago, United States Show map

Located approximately a 5-minute stroll from All Saints St Anthony Church, Bridgeport Bungalow Sleeps 4 Chicago offers a terrace and a dining table for guests' enjoyment. Offering Wi-Fi, the Chicago… More

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Downtown Chicago Stay With Free In & Out Parking 3

59 East Van Buren Street, Chicago, United States Show map

The spacious Downtown Chicago Stay With Free In & Out Parking 3 apartment is 7 minutes' walk from The Art Institute of Chicago and can accommodate up to 8 guests. This apartment is situated 1 km from… More

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Downtown Penthouse Lake Views Gym, Parking #1

2 East 8Th Street 2801, Chicago, United States Show map

Downtown Penthouse Lake Views Gym, Parking #1 Chicago apartment is a great place to stay in Printer's Row with roots dating back to the 1880s as the printing hub of America's Midwest, about a 20… More

From US$ 816 Book Now

Modern Chicago 2Br Retreat Parking + Patio

Apt. 3, 553 West 31St Street, Chicago, United States Show map

Located nearly 10 minutes' walk from Central Assembly of God Church, Modern Chicago 2Br Retreat Parking + Patio Villa offers quick access to various city attractions in the vicinity. Located in… More

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Mccormick Meetup - Prime Location - Sleeps 16

3338 South Calumet Avenue, Chicago, United States Show map

The spacious 242 m² Mccormick Meetup - Prime Location - Sleeps 16 Apartment Chicago is located within 6 km of Chicago Union train station and only 6 minutes' walk from the 1930s Supreme Life Building… More

From US$ 920 Book Now

Scott Ch

239 West Scott Street, Chicago, United States Show map

Scott Ch Apartment Chicago is nestled in the Near North Side district of Chicago, nearly 25 minutes' walk from the friendly Peggy Notebaert Nature Museum. Guests can use Wi-Fi for either business or… More

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Top Floor In The Heart Of West Town! Perfect For Any Group And Pet Friendly! Apts

1519 West Superior Street 2F, Chicago, United States Show map

Located in West Town with a busy stretch of West Chicago Avenue, dotted with New American restaurants and cafes, only a 7-minute walk from Lush Wine & Spirits, the 2-bedroom Top Floor In The Heart Of… More

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Downtown Guild Magnificent Mile, Gold Coast #4

215 East Chestnut Street 1604, Chicago, United States Show map

The spacious 1-bedroom Downtown Guild Magnificent Mile, Gold Coast #4 Apartment Chicago is nearly 5 minutes' walk from Loyola University Museum of Art and includes a fitness room. This 67 m²… More

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Loop 1Br W Deck Gym Wd Nr W Loop The L Chi-220

330 S Wells St, Chicago, Il 60606, Usa, Chicago, United States Show map

The 1-bedroom Loop 1Br W Deck Gym Wd Nr W Loop The L Chi-220 Apartment Chicago is located in Chicago Loop with an excellent range of restaurants in the neighbourhood that provide foods from all over… More

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Dwellish Rentals - Hyde Park Luxury Stay 5Br Near Lake & Uchicago

5017 South Drexel Boulevard, Chicago, United States Show map

Nestled just a 5-minute walk from Drexel Fountain, the spacious Dwellish Rentals - Hyde Park Luxury Stay 5Br Near Lake & Uchicago apartment offers quick access to numerous tourist attractions nearby.… More

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Hyde Park Penthouse

1364 East 48Th Street 3Rd Fl, Chicago, United States Show map

Located nearly a 10-minute walk from Muhammad Ali House, the spacious Hyde Park Penthouse Apartment Chicago is approximately 7 km from a top family-friendly place like the - art Shedd Indoor Aquarium… More

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Warm & Lovely 2Br Apt Close To Dining & Shops - Touhy 1S

1359 West Touhy Avenue Unit 1S, Chicago, United States Show map

Located around 15 km from Chicago Union railway station, the 70 m² Warm & Lovely 2Br Apt Close To Dining & Shops - Touhy 1S Chicago is only a 7-minute walk from Loyola Lakefront Park. More

From US$ 189 Book Now

W Loop Studio W Pool Gym Nr Restaurant Row Chi-264

939 W Washington Blvd, Chicago, Il 60607, Usa, Chicago, United States Show map

The 45 m² W Loop Studio W Pool Gym Nr Restaurant Row Chi-264 Chicago lies in a prime location in Chicago, around a 5-minute walk from Museum of Holography-Chicago. This 1-bedroom apartment is… More

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Stylish Cozy 2Br Apt Near Train Station Groceries

1612 West Beach Avenue, Chicago, United States Show map

The 2-bedroom Stylish Cozy 2Br Apt Near Train Station Groceries Chicago is located 4.3 km from Chicago Union train station and only 7 minutes' walk from Belmont Army Wicker Park. This 51 m² apartment… More

From US$ 246 Book Now

Designer 3Br Near Beach & Obama Center

6110 South Dorchester Avenue, Chicago, United States Show map

Designer 3Br Near Beach & Obama Center Chicago villa is located a mere 1.6 km from the Sprawling hands-on Museum of Science and Industry, giving access to various tourist spots nearby. More

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Landing Spectacular 2Bd Gym Rooftop Lounge

1922 W Ogden Ave, Chicago, United States Show map

Located in the Illinois Medical district 25 minutes' walk from Museum of Holography, the spacious Landing Spectacular 2Bd Gym Rooftop Lounge Chicago apartment accommodates up to 4 guests. Wi-Fi and… More

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Skyline Luxury 19Th Floor Retreat Near Grant Park

8 E 9Th St, Chicago, United States Show map

Skyline Luxury 19Th Floor Retreat Near Grant Park Apartment Chicago features a prime location a 19-minute walk from the 5 million US gal Shedd Aquarium and hosts up to 8 guests. This spacious 112 m²… More

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River North 1Br W Outdoor Pool 1 Block To L Chi-1035

411 West Chicago Avenue, Chicago, Il 60610, Us, Chicago, United States Show map

Situated nearly 25 minutes on foot from Skydeck Chicago, the 1-bedroom River North 1Br W Outdoor Pool 1 Block To L Chi-1035 Chicago apartment also boasts easy access to Chicago Union train station… More

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Group-Friendly 5Br Suite Near Mccormick - Sleeps 12

2036 South Michigan Avenue, Chicago, United States Show map

Located about a 5-minute walk from the indoor Wintrust Arena, the spacious Group-Friendly 5Br Suite Near Mccormick - Sleeps 12 Chicago is 2.4 km from a top family-friendly place like the - art Shedd… More

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870 1&2 - 2 Separate Suites In Same Building

870 North Orleans Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 186 m² 870 1&2 - 2 Separate Suites In Same Building Chicago, which is nearly 25 minutes' walk from the historic drawbridge "DuSable Bridge" and… More

From US$ 757 Book Now

W Loop 1Br W Pool Gym Nr Restaurant Row Chi-297

939 W Washington Blvd, Chicago, Il 60607, Usa, Chicago, United States Show map

The 1-bedroom W Loop 1Br W Pool Gym Nr Restaurant Row Chi-297 Apartment Chicago is located nearly 5 minutes on foot from Museum of Holography-Chicago and overlooks the city. The 58 m² apartment… More

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Skyline 24Th Floor Near Grant Park

8 East 9Th Street, Chicago, United States Show map

The spacious Skyline 24Th Floor Near Grant Park Apartment Chicago is situated in Downtown Chicago, which is exploding with culture, art, cuisine, architecture and fashion, 20 minutes' walk from… More

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1Br Tranquil Hyde Park Apartment - Harper 202 & 402 Rep

5345 South Harper Avenue, Chicago, United States Show map

Rockefeller Memorial Chapel is only 1.8 km from the 1-bedroom 1Br Tranquil Hyde Park Apartment - Harper 202 & 402 Rep Chicago, while Akira is situated nearby. More

From US$ 237 Book Now

Gold Coast Convertible W Lounge Nr Oak St Chi-83

1 E Delaware Pl, Chicago, Il 60611, Usa, Chicago, United States Show map

Situated only 1.4 km from Chicago-style pizza, Gold Coast Convertible W Lounge Nr Oak St Chi-83 Chicago apartment provides guests with Wi-Fi for either business or leisure. The spacious apartment has… More

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Landing Modern 2Bd Clubhouse Gym

8900 Archer Ave, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 4-room Landing Modern 2Bd Clubhouse Gym Apartment Chicago, which is within 7 km of Indian Prairie Public Library District and about a 10-minute ride… More

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Chic River North Condo 2Br 2Ba With Private Balcony

312 West Grand Avenue, Chicago, United States Show map

Set in the Theatre district, a 25-minute walk from the Oak Magnificent Mile Street, the spacious Chic River North Condo 2Br 2Ba With Private Balcony Chicago accommodates up to 5 guests. At this… More

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5 Mi To Midway: Walkable Chicago Apartment

8136 S Kedzie Ave Unit 202, Chicago, United States Show map

Situated approximately a 25-minute stroll from 50-Acre Park, the spacious 130 m² 5 Mi To Midway: Walkable Chicago Apartment also boasts easy access to Chicago Union train station which is 16 km away.… More

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Blueground Greektown Bbq Gym Nr Willis Tower Chi-1255

West Adams Street 812, Chicago, United States Show map

Set about a 25-minute walk from Macy's on State Street, the 65 m² Blueground Greektown Bbq Gym Nr Willis Tower Chi-1255 Apartment Chicago comprises a balcony overlooking the city. This 1-bedroom… More

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River N 2Br W Gym Wd Bbq Pool Nr Mag Mile Chi-132

8 E Huron St, Chicago, Il 60611, Usa, Chicago, United States Show map

Located 0.7 km from the skyscraper 360 Chicago Observation Deck, the 50 m² River N 2Br W Gym Wd Bbq Pool Nr Mag Mile Chi-132 Chicago apartment accommodates up to 2 guests. The apartment is situated 2… More

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Lux Dtown Penthouses 9Bd-9Ba Sleep 25 Parking, Pool, Gym

2 E 8Th St #2801, Chicago, Il 60605, Chicago, United States Show map

Featuring a prime location, the spacious 9-bedroom Lux Dtown Penthouses 9Bd-9Ba Sleep 25 Parking, Pool, Gym Chicago apartment offers views of the lake, about 25 minutes' walk from the 91 - acre man -… More

From US$ 5808 Book Now

Loop 1Br W Pool Gym Nr The L Riverwalk Chi-242

210 N Wells St, Chicago, Il 60606, Usa, Chicago, United States Show map

The spacious Loop 1Br W Pool Gym Nr The L Riverwalk Chi-242 Chicago apartment is nestled in Streeterville with a continual thrum of cabs and buses connecting people to other parts of the city, just… More

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