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2026-11-09
2026-11-10
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Hotels in Kayak Chicago area of Illinois

Flexhome Ukrainian Village - 2Br - Convenient Walkability

906 N Damen 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, within a 500-metre distance of Mariano's, Flexhome Ukrainian Village - 2Br… More

From US$ 290 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

Suite 2 On Southport 4 Queen Beds

2501 North Southport Avenue, Chicago, United States Show map

Situated around 500 metres from Saint Josaphat Catholic Church, Suite 2 On Southport 4 Queen Beds Chicago villa offers easy access to numerous tourist spots in the area. More

From US$ 614 Book Now

Suite 1 On Southport 4 Queen Beds

2501 North Southport Avenue, Chicago, United States Show map

Situated a 6-minute walk from Saint Josaphat Catholic Church, Suite 1 On Southport 4 Queen Beds Chicago offers proximity to various nearby tourist attractions. More

From US$ 141 Book Now

Trendy West Town Flat - 2 Bed / 1.5 Bath W Parking

1836 West Superior Street 1F, Chicago, United States Show map

The spacious 2-bedroom Trendy West Town Flat - 2 Bed / 1.5 Bath W Parking Apartment Chicago is located 3.4 km from Chicago Union train station and around 5 minutes' walk from Chicago Truborn. This… More

From US$ 283 Book Now

Walk To Blue Line: Sleek Apartment In Bucktown!

2113 W Armitage Ave Unit 1R, Chicago, United States Show map

The 2-bedroom Walk To Blue Line: Sleek Apartment In Bucktown! Chicago is located 2.9 km from Oz Public Park and approximately a 25-minute walk from the private DePaul Catholic University. At the… More

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Flexhome Wicker Park 3Br Dv1

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

Flexhome Wicker Park 3Br Dv1 Chicago apartment is located in Wicker Park, which regularly seduces top-notch, innovative restaurateurs and mixologists, and Damen tube station is just 0.8 km away. More

From US$ 327 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

Flexhome Wicker Park - Stylish 2Br - Sleeps 6

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

The spacious 2-bedroom Flexhome Wicker Park - Stylish 2Br - Sleeps 6 Chicago apartment is located 4.1 km from Chicago Union train station and nearly a 5-minute walk from Holy Trinity Orthodox… More

From US$ 629 Book Now

Wicker Park 2Br Modern Apartment Dv3

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

Wicker Park 2Br Modern Apartment Dv3 Chicago offers proximity to such tourist attractions as Holy Trinity Orthodox Cathedral, situated approximately 5 minutes' walk away. More

From US$ 184 Book Now

4 Bedroom • Theater Room • Gym • Walk To Lincoln Park!

210 W St Paul Ave, Chicago, Il 60614, Usa, Chicago, United States Show map

The 4-bedroom 4 Bedroom • Theater Room • Gym • Walk To Lincoln Park! Chicago villa offers swift access to various city sites, such as the non - denominational Moody Church, situated only 6 minutes'… More

From US$ 490 Book Now

Cozy & Modern 3Br Apartment - Division 201W 301W Rep

2153 West Division Street Apt 201W, Chicago, United States Show map

The 88 m² Cozy & Modern 3Br Apartment - Division 201W 301W Rep Chicago offers easy entry to such city sights as Holy Trinity Orthodox Cathedral, situated approximately a 5-minute walk away. This 1… More

From US$ 506 Book Now

The Picasso On Lincoln Park

1856 North Lincoln Avenue Unit #3, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at The Picasso On Lincoln Park Apartment Chicago, which is around a 10-minute drive from the baseball stadium "Wrigley Field" and just 0.8 km from Saint… More

From US$ 325 Book Now

Two Bedroom West Loop

1142 West Grand Avenue, Chicago, United States Show map

Located approximately a 25-minute walk from the lit 1926 theater "Cadillac Palace Theatre", the 2-bedroom Two Bedroom West Loop Chicago apartment is 4.4 km from a top family-friendly place like the… More

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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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Stunning 5Br Home In Heart Of Chicago With 2 Rooftops

1307 North Bell Avenue, Chicago, United States Show map

Located within a 6-km distance of the skyscraper 360 Chicago Observation Deck, the 5-bedroom Stunning 5Br Home In Heart Of Chicago With 2 Rooftops offers a casino for guests' entertainment. Offering… More

From US$ 1501 Book Now

Updated 1 Bedroom In The Best Location!

1649 North Wells Street 1A, Chicago, United States Show map

The 1-bedroom Updated 1 Bedroom In The Best Location! Chicago apartment is located in Lincoln Park with a unique mix of bars, restaurants, and entertainment spots only 5 minutes on foot from Chicago… More

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Luxe 4Br With Hot Tub & Game Room

1654 West Ohio Street, Chicago, United States Show map

Luxe 4Br With Hot Tub & Game Room Chicago villa is located within 4 km of Millennium Public Park, giving access to various tourist spots nearby. More

From US$ 967 Book Now

Walker'S Paradise 1Br Apartment In Lincoln Park - Lincoln 2501

2501 North Lincoln Avenue, Chicago, United States Show map

The 1-bedroom Walker'S Paradise 1Br Apartment In Lincoln Park - Lincoln 2501 Chicago is nestled in Lincoln Park with cafés and boutique shops, within 25 minutes' walk of the 35 - acre Lincoln Park… More

From US$ 64 Book Now

3-Story Townhome Free Parking Private Patio Washer-Dryer

344 West Dickens Avenue, Chicago, United States Show map

Offering a casino for a delightful experience, 3-Story Townhome Free Parking Private Patio Washer-Dryer Chicago villa is located merely an 8-minute walk from the botanical garden "Lincoln Park… More

From US$ 447 Book Now

Beautiful Remodeled Penthouse Unit In Old Town

1556 North La Salle Street, Chicago, United States Show map

Located merely 1.3 km from the free Lincoln Park Zoo, the comfortable Beautiful Remodeled Penthouse Unit In Old Town Hotel Chicago is about a 5-minute walk from Second City. The hotel also provides… More

From US$ 139 Book Now

Mtm Fully Furnished Rental In Old Town - 2 Beds

1556 North La Salle Drive, Chicago, United States Show map

Located in Old Town with roots dating back to the mid-19th century, 5 minutes' walk from the non - denominational Moody Church, the spacious Mtm Fully Furnished Rental In Old Town - 2 Beds Chicago… More

From US$ 299 Book Now

Mtm Fully Furnished Rental In Old Town - 2 Beds

1556 North La Salle Street, Chicago, United States Show map

The spacious 88 m² Mtm Fully Furnished Rental In Old Town - 2 Beds Chicago apartment is located in Near North Side, which is home to iconic skyscrapers like the 1920s Wrigley Building, as well as 360… More

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Cozy, Top-Floor 3Br Loft With Balcony In West Town

518 North Ashland Avenue, Chicago, United States Show map

To enjoy your vacation in Chicago, stay at Cozy, Top-Floor 3Br Loft With Balcony In West Town Chicago apartment, which is about 10 minutes by car from Macy's on State Street and around 7 km from the… More

From US$ 347 Book Now

Level Chicago Old Town

1140 North Wells Street, Chicago, United States Show map

The elegant Level Chicago Old Town Hotel enjoys a prime location approximately 25 minutes' walk from family-friendly attractions like the 35 - acre Lincoln Park Zoo. Boasting a heated pool and a… More

From US$ 206 Book Now

Hotel Lincoln

1816 North Clark Street, Chicago, United States Show map

Featuring 184 rooms, the smoke-free Hotel Lincoln Chicago is located near an entertainment district and merely 6 minutes' walk from Chicago History Museum. The hotel offers 24-hour desk and wake-up… More

From US$ 590 Book Now

Hotel Lincoln

1816 N Clark Street, Chicago, United States Show map

Offering 193 rooms, the 4-star smoke-free Hotel Lincoln Chicago is near the beach district of Chicago, within 15 minutes' walk of Oz Public Park. The hotel is located within reach of Chicago History… More

From US$ 112 Book Now

Ukrainian Village 2 Bd 2Ba - Steps From Division Condo

1054 N Leavitt G, Chicago, United States Show map

Situated approximately a 10-minute ride from Eckhart Park, the spacious 80 m² Ukrainian Village 2 Bd 2Ba - Steps From Division Condo Chicago also boasts easy access to Chicago Union train station… More

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Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof Ev Tesla

467 North Armour Street, Chicago, United States Show map

Boasting a sundeck and a play area, the 3-bedroom Art Downtown Fulton Market Entire 3 Bedroom Home Sleep10 Private Garage Roof Ev Tesla Chicago is suitable for up to 12 guests and is located in West… More

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870 Bldg - 3 Separate Suites In Same Building

870 North Orleans Street, Chicago, United States Show map

The spacious 279 m² 870 Bldg - 3 Separate Suites In Same Building Chicago is located in Near North Side, which is home to iconic skyscrapers like the 1920s Wrigley Building, as well as 360 Chicago, a… More

From US$ 2390 Book Now

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

Webster House

402 W. Webster, Chicago, United States Show map

The 58 m² Webster House Apartment Chicago offers easy access to such tourist sites as Lincoln Monument, located about a 5-minute walk away. 3.2 km from the baseball stadium "Wrigley Field", this 1… More

From US$ 230 Book Now

Cozy Beautiful Downtown Unit Chi In Prime River North Location Near Mag Mile - 2

North Orleans Street 870, Chicago, United States Show map

The spacious 2-bedroom Cozy Beautiful Downtown Unit Chi In Prime River North Location Near Mag Mile - 2 Chicago apartment is approximately 25 minutes' walk from the public Cloud Gate Sculpture. Wi-Fi… More

From US$ 189 Book Now

Cozy Beautiful Downtown Unit Chi In Prime River North Location Near Mag Mile - 1

North Orleans Street 870, Chicago, United States Show map

The 2-bedroom Cozy Beautiful Downtown Unit Chi In Prime River North Location Near Mag Mile - 1 Chicago apartment is nearly a 25-minute walk from the super - tall skyscraper "Willis Tower". This… More

From US$ 583 Book Now

Beautiful Unit Chi In Prime River North - Top Floor

870 North Orleans Street, 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 The Art Institute of… More

From US$ 1132 Book Now

Luxury Downtown Penthouse With Private Rooftop

858 North Orleans Street #Ph, Chicago, United States Show map

Located 25 minutes' walk from The Art Institute of Chicago, the spacious Luxury Downtown Penthouse With Private Rooftop Chicago apartment overlooks the city. The maximum occupancy at this apartment… More

From US$ 538 Book Now

The Orleans Floor 3 Private Rooftop Deck

858 North Orleans Street #Rtd3, Chicago, United States Show map

Overlooking the city, the spacious 4-bedroom The Orleans Floor 3 Private Rooftop Deck Chicago apartment is approximately 20 minutes' walk from Oak Street Beach in Chicago. The apartment offers modern… More

From US$ 1218 Book Now

The Orleans - Entire Building - With Rooftop Deck

858 North Orleans Street, Chicago, United States Show map

The spacious 446 m² The Orleans - Entire Building - With Rooftop Deck Chicago apartment lies around a 10-minute ride from the large Grant Urban Park and around 800 metres from Chicago tube station. More

From US$ 2609 Book Now

River North 1Br Nr L Stop Riverwalk Loop Chi-1037

751 North Hudson Avenue, Chicago, Il 60610, Us, Chicago, United States Show map

The spacious 62 m² River North 1Br Nr L Stop Riverwalk Loop Chi-1037 Chicago apartment lies within a 2-km distance of the huge outdoor Cloud Gate Sculpture and nearly 15 minutes on foot from Chicago… More

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River North 1Br W Pool Fitness 1 Block To L Chi-1039

751 North Hudson Avenue, Chicago, Il 60610, Us, Chicago, United States Show map

Featuring a prime location a 6-minute walk from the modest Ward A. Montgomery Park, the 59 m² River North 1Br W Pool Fitness 1 Block To L Chi-1039 Chicago apartment accommodates up to 2 guests. This… More

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Beautifully Remodeled Flat Downtown #3N

858 North Orleans Street #3N, Chicago, United States Show map

Beautifully Remodeled Flat Downtown #3N Villa Chicago offers proximity to nearby tourist spots, such as the Oak Magnificent Mile Street, situated a mere 1.5 km away. More

From US$ 239 Book Now

River North 1Br Nr Riverwalk W Yoga Studio Chi-1040

751 North Hudson Avenue, Chicago, Il 60610, Us, Chicago, United States Show map

The 1-bedroom River North 1Br Nr Riverwalk W Yoga Studio Chi-1040 Chicago lies 2.3 km from The Art Institute of Chicago and approximately a 5-minute drive from Chicago tube station. The 60 m²… More

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Grand House 424

840 West Grand Avenue 2, Chicago, United States Show map

The comfortable Grand House 424 Hostel Chicago, located 3.6 km from the 35 - acre Lincoln Park Zoo, features Wi-Fi in public areas. Offering luggage storage, this Chicago hostel is located in West… More

From US$ 88 Book Now

Beautifully Remodeled Second Floor Flat In River North With Private Rooftop - 2S

North Orleans Street 858, Chicago, United States Show map

Featuring a convenient location, the 2-bedroom Beautifully Remodeled Second Floor Flat In River North With Private Rooftop - 2S Chicago offers views of the city, nearly a 20-minute walk from the… More

From US$ 662 Book Now

Beautifully Remodeled Second Floor Flat In River North - 2N

North Orleans Street 858, Chicago, United States Show map

The spacious 112 m² Beautifully Remodeled Second Floor Flat In River North - 2N Chicago features a prime location just 1.6 km from the skyscraper 360 Chicago Observation Deck and hosts up to 10… More

From US$ 539 Book Now

Beautifully Remodeled Third Floor Flat In River North - 3N

North Orleans Street 858, Chicago, United States Show map

The spacious 112 m² Beautifully Remodeled Third Floor Flat In River North - 3N Chicago features a convenient location nearly 25 minutes' walk from The Art Institute of Chicago and hosts up to 10… More

From US$ 283 Book Now

The Orleans - Floor 2 Private Roof Deck Patio

858 North Orleans Street, Chicago, United States Show map

Featuring a convenient location just 6 minutes' walk from the long-standing Carl Hammer Gallery, the spacious 4-bedroom The Orleans - Floor 2 Private Roof Deck Patio Apartment Chicago accommodates up… More

From US$ 2173 Book Now

Landing At Next - Studio In Near North Side

347 W Chestnut St # 2506 Chicago, Il 60610, Chicago, United States Show map

Set 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 The Chicago Theatre, Landing… More

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Boho City Escape Parking Balcony

545 North Wood Street, Chicago, United States Show map

The 2-bedroom Boho City Escape Parking Balcony Chicago apartment is located in West Town with a busy stretch of West Chicago Avenue, dotted with New American restaurants and cafes, and Ashland tube… More

From US$ 854 Book Now

The Boho House Two Private Suites Parking

545 North Wood Street, Chicago, United States Show map

The spacious The Boho House Two Private Suites Parking Chicago is a great place to stay in West Town with a busy stretch of West Chicago Avenue, dotted with New American restaurants and cafes, a 15… More

From US$ 850 Book Now