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

Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access

1335 North Greenview Avenue 1F, Chicago, United States Show map

Situated about a 5-minute walk from St. Stanislaus Kostka Church, the 46 m² Wicker Park 1-Br Walk To Train & Grocery Easy Downtown Access Apartment Chicago offers guests easy access to various… More

From US$ 243 Book Now

Flexhome Ukrainian Village • 2Br • Convenient Walkability - Sleeps 6

906 N Damen Ave, Chicago, Il 60622, Chicago, United States Show map

The spacious 65 m² Flexhome Ukrainian Village • 2Br • Convenient Walkability - Sleeps 6 Chicago apartment provides easy access to various city attractions, such as Mariano's, situated only a 6-minute… More

From US$ 276 Book Now

Flexhome East Village - Modern 2Br - Quiet Street

846 N Hermitage Ave, Chicago, Il 60622, Usa, Chicago, United States Show map

Located in West Town with a busy stretch of West Chicago Avenue, dotted with New American restaurants and cafes, about 5 minutes' walk from RR #1 Chicago, the spacious 2-bedroom Flexhome East Village… More

From US$ 284 Book Now

Modern 3Br Apt Near United Center

3345 West Douglas Boulevard 3, Chicago, United States Show map

The 3-bedroom Modern 3Br Apt Near United Center Chicago is located around 7 km from Chicago Union train station and just a 6-minute walk from Greater Open Door M.b. Church. Boasting a Jacuzzi, this… More

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Tranquil Library 2Brm 1Bath Private Eclectic Apt At Solar Lodge

4419 North Christiana Avenue, Chicago, United States Show map

The 167 m² Tranquil Library 2Brm 1Bath Private Eclectic Apt At Solar Lodge Chicago is located just a 5-minute walk from Christ Evangelical Lutheran Church and 3.1 km from Architectural Artifacts. More

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Modern 1Br W/ Workspace Near O'Hare

5105 North East River Road, Chicago, United States Show map

A prime location of the 56 m² Modern 1Br W/ Workspace Near O'Hare Chicago apartment provides easy access to Donald E Stephens Convention Center 2.6 km away. The apartment is situated a 40-minute ride… More

From US$ 174 Book Now

Condo Apartment Near Midway Airport

5470 South Archer Avenue 1A, Chicago, United States Show map

Situated nearly a 10-minute drive from Hawthorne Park District, the 1-bedroom Condo Apartment Near Midway Airport Chicago also boasts easy access to Chicago Union train station which is 13 km away. More

From US$ 167 Book Now

Downtown 3Bd Penthouse Lake Mich Views Plus Gym 13

820 South Michigan Avenue 1213, Chicago, United States Show map

Situated merely 1.4 km from the indoor public Shedd Aquarium, the spacious 3-bedroom Downtown 3Bd Penthouse Lake Mich Views Plus Gym #13 Chicago apartment can host up to 6 guests in Chicago. Wi-Fi is… More

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The Banksy-Greystone Rooftop Firepit United Center

2320 W Jackson Blvd, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 2-bedroom The Banksy-Greystone Rooftop Firepit United Center Chicago apartment, which is 2.8 km from the 184-acre Garfield Park Conservatory… More

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Secret Gallery On The Park - 2Bd/1Ba

870 North Franklin Street #1, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 2-bedroom Secret Gallery On The Park - 2Bd/1Ba Chicago apartment, which is just 1.7 km from the fancy high-rise Shops at Northbridge Mall and… More

From US$ 875 Book Now

5 Mi To Dtwn: Ukrainian Village Apartment!

2148 W Chicago Ave Unit 2, Chicago, United States Show map

The spacious 2-bedroom 5 Mi To Dtwn: Ukrainian Village Apartment! Chicago is located 4.1 km from Chicago Union train station and only 7 minutes' walk from Ukrainian Institute of Modern Art. This 93… More

From US$ 274 Book Now

Regal Stylish Uptown Loft Beachfront Rooftop 13 Mins Dt 4 Mins Lake

1049 West Lawrence Avenue 704, Chicago, United States Show map

Situated around a 25-minute stroll from the baseball stadium "Wrigley Field", the 1-bedroom Regal Stylish Uptown Loft Beachfront Rooftop 13 Mins Dt 4 Mins Lake Chicago apartment also boasts easy… More

From US$ 119 Book Now

Stylish Friendly 3Br Suite Near Mccormick

2001 South State Street, Chicago, United States Show map

Situated about 25 minutes' walk from Buckingham Fountain, the 3-bedroom Stylish Friendly 3Br Suite Near Mccormick Chicago can host up to 7 guests in Chicago. The apartment offers modern facilities… More

From US$ 848 Book Now

Downtown Chicago Stay With Free In & Out Parking 6

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

To enjoy your vacation in Chicago, stay at the spacious 67 m² Downtown Chicago Stay With Free In & Out Parking 6 apartment, which is within 20 minutes' walk of the premier natural-history Field… More

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3Br Modern Apt • Gym • Workspace • Quiet Location

3656 North Osage Avenue Unit 2, Chicago, United States Show map

3Br Modern Apt • Gym • Workspace • Quiet Location Chicago features a prime location a 10-minute drive from Donald E Stephens Convention Center and hosts up to 9 guests. This apartment is situated 18… More

From US$ 267 Book Now

West Loop - City Views With In & Out Parking 6

315 South Peoria Street, Chicago, United States Show map

Located in West Loop with must-visit spots for foodies, eclectic art galleries and shops, and numerous acres of redeveloped park space an 18-minute walk from Money Museum at the Federal Reserve Bank,… More

From US$ 696 Book Now

Location! Location! 2Bd 1Bth Spacious Apartment!

2547 South Wallace Street 2R, Chicago, United States Show map

The 2-bedroom Location! Location! 2Bd 1Bth Spacious Apartment! Chicago lies within a 3-km distance of the premier natural-history Field Museum and just 600 metres from Halsted tube station. The 48 m²… More

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Spacious Downtown Penthouse Vintage, Balcony, Gym 3

731 S Plymouth Ct #803, Chicago, 60605, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 1-bedroom Spacious Downtown Penthouse Vintage, Balcony, Gym 3 Chicago apartment, which is only 1.6 km from the premier natural-history Field Museum and… More

From US$ 921 Book Now

Downtown Penthouse 01 Vintage 2Bd Gym

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

The spacious 94 m² Downtown Penthouse 01 Vintage 2Bd Gym Chicago apartment lies only 1.6 km from the premier natural-history Field Museum and about a 5-minute ride from Harrison tube station. Guests… More

From US$ 397 Book Now

The Roscoe Village Guesthouse

2009 West Roscoe Street, Chicago, United States Show map

The 3-bedroom The Roscoe Village Guesthouse Chicago is located in the Roscoe Village district of Chicago, approximately a 5-minute walk from Fellger Park. The 130 m² apartment features Wi-Fi, along… More

From US$ 162 Book Now

4 Bedroom Sleeps 20 People

1432 West 21St Street, Chicago, United States Show map

The 167 m² 4 Bedroom Sleeps 20 People Chicago apartment lies in a convenient location in Chicago, 500 metres from Mole de Mayo. This 4-bedroom apartment is situated 3.6 km from Chicago Union train… More

From US$ 499 Book Now

Mich Ave Downtown, Park, Museums 2Bd 4

1212 South Michigan Avenue 401, Chicago, United States Show map

Located in Downtown Chicago, which is an amazing shopping destination lined with stores, boutiques, galleries and retail centers, only a 6-minute walk from Statue of Christopher Columbus, the 2… More

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West Loop - City Views With In & Out Parking 5

315 South Peoria Street, Chicago, United States Show map

The spacious 4-bedroom West Loop - City Views With In & Out Parking 5 Chicago apartment is located in West Loop with great dining and entertainment, around 5 minutes' walk from the 1.4 - acre Mary… More

From US$ 1406 Book Now

Bootlegger House Sleeps 10-20 Free Tv & Parking

3153 North Pine Grove Avenue, Chicago, United States Show map

Set in Lakeview, which is one of the 77 community areas of Chicago, Illinois, a 25-minute walk from Graceland Cemetery, the spacious Bootlegger House Sleeps 10-20 Free Tv & Parking Apartment Chicago… More

From US$ 1435 Book Now

The Brown House - A Luxurious Uchicago Campus Stay

6138 South Ingleside Avenue Unit 1, Chicago, United States Show map

Spacious 3-bedroom The Brown House - A Luxurious Uchicago Campus Stay offers a prime location, around 5 minutes' walk from Lorado Taft's Midway Studios. The apartment offers modern facilities, such… More

From US$ 542 Book Now

Cozy 3Br City Living In South Loop Near Mccormick Place, Soldier Field & Lakefront

2036 South Michigan Avenue Unit 202, Chicago, United States Show map

The 104 m² Cozy 3Br City Living In South Loop Near Mccormick Place, Soldier Field & Lakefront Chicago apartment is a great place to stay in South Loop, set including historic Printers Row, 14… More

From US$ 512 Book Now

Near Zoo & Beach • Reading Nook + Parking

West Fullerton Avenue 716, Chicago, United States Show map

Featuring a prime location nearly 5 minutes' walk from the midsize live music venue "Lincoln Hall", the spacious 3-bedroom Near Zoo & Beach • Reading Nook + Parking Chicago apartment accommodates up… More

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Peaceful Beachfront Loft Rooftop Gym

1049 West Lawrence Avenue Apt 804, Chicago, United States Show map

Featuring a prime location a 5-minute walk from Byline Bank Aragon Ballroom, Peaceful Beachfront Loft Rooftop Gym Chicago apartment accommodates up to 2 guests. This apartment is situated 11 km from… More

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Charming 2Br Apartment With Skyline View, Optional Parking & Gym Access Near Mccormick Place, Lakefront And Soldier Field

2036 South Michigan Avenue Unit 411, Chicago, United States Show map

Located nearly 5 minutes' walk from the indoor Wintrust Arena, the spacious 2-bedroom Charming 2Br Apartment With Skyline View, Optional Parking & Gym Access Near Mccormick Place, Lakefront And… More

From US$ 808 Book Now

Bright 2Bed 2Bath In Brand New Pilsen Development

2354 West Polk Street, Chicago, United States Show map

Set 2.5 km from the modern United Center Arena, the 2-bedroom Bright 2Bed 2Bath In Brand New Pilsen Development Apartment Chicago comprises a patio and a balcony overlooking the city. The spacious… More

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Spacious 3 Bedroom Apt Near Downtown

2418 West Grenshaw Street Unit 1, Chicago, United States Show map

Situated approximately a 10-minute stroll from Western underground station, the 2-bedroom Spacious 3 Bedroom Apt Near Downtown Chicago offers Wi-Fi for business or leisure needs. Enjoying a prime… More

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Steps From The Lake Edgewater Modern 2Bd 2Ba

6044 North Winthrop Avenue, Chicago, United States Show map

Featuring a prime location, the 93 m² Steps From The Lake Edgewater Modern 2Bd 2Ba Chicago apartment offers views of the lake, and is a 16-minute walk from the energetic urban Kathy Osterman Beach. More

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Luxury Cozy 2Br With Optional Parking And Gym Access Near Mccormick Place, Lakefront And Soldier Field

2036 South Michigan Avenue Unit 709, Chicago, United States Show map

Featuring a lift and a vending machine, the spacious 3-bedroom Luxury Cozy 2Br With Optional Parking And Gym Access Near Mccormick Place, Lakefront And Soldier Field Chicago apartment is nearly 5… More

From US$ 785 Book Now

Boulevard Stays Walk Everywhere 5 Mins To Magnificent Mile River North 05

707 North Wells Street, Chicago, United States Show map

The 74 m² Boulevard Stays Walk Everywhere 5 Mins To Magnificent Mile River North 05 Chicago apartment, located in River North with luxe shops and eateries, plus posh nightclubs and cocktail bars… More

From US$ 568 Book Now

Comfy Garden Suite In Andersonville

5315 North Glenwood Avenue, Chicago, United States Show map

Situated about 7 km from the 35-acre beautifully landscaped Lincoln Park Zoo, the 84 m² Comfy Garden Suite In Andersonville Chicago can host up to 2 guests in Chicago. Wi-Fi and parking are also… More

From US$ 191 Book Now

Modern 3Br King Chicago Stay Near United Center

3211 W Le Moyne St, Chicago, United States Show map

Situated nearly a 15-minute ride from the baseball stadium "Wrigley Field", the spacious 130 m² Modern 3Br King Chicago Stay Near United Center apartment also boasts easy access to Chicago Union… More

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Cozy 1 Bedroom Apt Near Logan Sq

2324 North California Avenue, Chicago, United States Show map

The 1-bedroom Cozy 1 Bedroom Apt Near Logan Sq Chicago lies just 1.8 km from The Dill Pickle Food Co-op and approximately 200 metres from California tube station. The apartment is situated around a… More

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Wabash 4Br - Pool Free In & Out Parking 2

626 South Wabash Avenue, Chicago, United States Show map

Wabash 4Br - Pool Free In & Out Parking 2 Apartment Chicago lies only 1.8 km from the Metropolitan Civic Opera House and around a 5-minute drive from Harrison tube station. The spacious apartment is… More

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The Bright Retreat In Andersonville

1343 West Winona Street 1W, Chicago, United States Show map

Located around 700 metres from Argyle Street, the 1-bedroom The Bright Retreat In Andersonville Chicago apartment is within a 7-km distance of a top family-friendly place like the 35 - acre Lincoln… More

From US$ 253 Book Now

Wrigleyville Art Deco Retreat Garage

1128 West Addison Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 3-bedroom The Addison Art Deco Executive Retreat Garage Apartment Chicago, which is within 10 minutes' drive of the 35-acre beautifully… More

From US$ 1326 Book Now

2Br Garden Suite In Lakeview Walk To Wrigley

902 W Newport Ave, Chicago, United States Show map

The spacious 79 m² 2Br Garden Suite In Lakeview Walk To Wrigley Chicago is a good choice for accommodating up to 5 guests, offering a prime setting just 0.9 km from the baseball stadium "Wrigley… More

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City Retreat

10601 South Edbrooke Avenue Unit 2, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 84 m² City Retreat Chicago apartment, which is within 20 minutes' walk of A. Philip Randolph Pullman Porter Museum and approximately 2 km from… More

From US$ 124 Book Now

North Chicago Spacious Home

5808 North Winthrop Avenue, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the 4-bedroom North Chicago Spacious Home apartment, which is merely 550 metres from Saint Andrew's Greek Orthodox Church and just 0.7 km from Emanuel… More

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East Lincoln Park Gem Spacious 4 Br

650 West Wrightwood Avenue G, Chicago, United States Show map

The 232 m² East Lincoln Park Gem Spacious 4 Br Chicago apartment boasts views of the garden and is located 25 minutes' walk from North Avenue Beach. The apartment features Wi-Fi, along with parking… More

From US$ 359 Book Now

Wabash 4Br - Pool Free In & Out Parking 1

626 South Wabash Avenue, Chicago, United States Show map

Located in the South Loop district, the spacious Wabash 4Br - Pool Free In & Out Parking 1 Apartment Chicago is only 10 minutes' walk from Buckingham Fountain and 2.7 km from the third-smallest… More

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Livn Millennium Park Downtown Chicago Prem Studio

19 South Wabash Avenue, Chicago, United States Show map

Located in the Theatre district of Chicago approximately 25 minutes' walk from the 1924 open-air stadium "Soldier Field", the 3-room Livn Millennium Park Downtown Chicago Prem Studio accommodates up… More

From US$ 487 Book Now

Closest Condo To The United Center 3 Bedrooms & Futon

2212 West Monroe Street, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 130 m² Closest Condo To The United Center 3 Bedrooms & Futon Chicago, which is 4.8 km from Chicago Cultural Center and around a 10-minute drive… More

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Walk To The Beach • Private Office • 5Br

1220 W Columbia Ave, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at the spacious 158 m² Walk To The Beach • Private Office • 5Br Chicago apartment, which is within 25 minutes' walk of Touhy Park and just 1.6 km from Jarvis… More

From US$ 386 Book Now

Sheridan Park Stunner! No Matter If You Are In Town For Business Or Fun This Property Has You Covered Apts

4421 North Clark Street 205, Chicago, United States Show map

Situated around a 15-minute drive from the free Lincoln Park Zoo, Sheridan Park Stunner! No Matter If You Are In Town For Business Or Fun This Property Has You Covered Apts Chicago apartment also… More

From US$ 313 Book Now

Garden Apt Private Patio Fire Pit Pets Ok

851 North Fairfield Avenue, Chicago, United States Show map

Situated 6 minutes' walk from Komoda Gift Shop, Garden Apt Private Patio Fire Pit Pets Ok Chicago offers proximity to various nearby tourist attractions. The maximum occupancy at this spacious 74 m²… More

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