Places to stay in Chicago, IL

11918 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • premierinn
  • sykescottages
  • plumguide
  • hotelscom
  • tripadvisor
  • homestay
  • tuivillas
  • hostelworld
Chicago, IL place to stay
Choose the perfect holiday accommodation
Price per night
Accommodation type
Rating

11918 Best places to stay in Chicago, IL

Ideal Lincoln Park Studio W/ W/d & Lounge, 2 Blocks From L, By Blueground - Chicago, IL
Chicago, IL
01/01 – 31/12
6 €/nighttotal: 2184 € (364 )

Ideal Lincoln Park Studio W/ W/d & Lounge, 2 Blocks From L, By Blueground

1 2
studio, Chicago
This modern studio apartment is situated in Goose Island, Chicago, offering proximity to Lake Michigan and Millennium Park, with convenient access to the Chicago History Museum and Chicago Theatre.
This 34 square meter flat accommodates two guests and features a fully equipped kitchen with a fridge and microwave, air conditioning, in-apartment laundry facilities, and premium amenities including a smart TV.
Homey 2br Apt W/ Parking - Chicago, IL
9.1 37 reviews
Chicago, IL
06/07 – 28/07
183 €/nighttotal: 4026 € (22 )

Homey 2br Apt W/ Parking

1 3
apartment, Chicago
This Chicago apartment rental sleeps four guests in two bedrooms with queen-size beds, each featuring a fridge and microwave, and offers free Wi-Fi and one parking space; the precise location within Chicago is not specified, preventing details on proximity to landmarks.
The fully furnished flat includes a complete kitchen, a living room with a TV and sofa, and a small dining area, making it suitable for short or long stays.
Quirky Quarters At Wrigley - Chicago, IL
9.9 229 reviews
Chicago, IL
09/08 – 13/08
188 €/nighttotal: 752 € (4 )

Quirky Quarters At Wrigley

1 2
apartment, Chicago
This ground-floor flat in Chicago's Lakeview neighbourhood is a 0.6km walk from Wrigley Field and 0.2km from the Southport Corridor, offering easy access to the Brown and Red lines.
The one-bedroom, one-bathroom apartment sleeps two, features a fully equipped kitchen including a dishwasher, air conditioning, and free membership to The Metropolitan co-working space in the Willis Tower; nearby attractions include the Music Box Theatre and Metro Theatre.
Stylish 2-br In Avondale Near Logan Square/wrigley - Chicago, IL
9.9 57 reviews
Chicago, IL
29/08 – 05/09
147 €/nighttotal: 1029 € (7 )

Stylish 2-br In Avondale Near Logan Square/wrigley

2 1
apartment, Chicago
This Avondale flat, near Logan Square in Chicago, is within walking distance of three Blue Line stations and offers easy access to I-90/94.
The two-bedroom, one-bathroom apartment sleeps four, features a fully equipped kitchen including a dishwasher, and boasts original wood floors in a classic 1896 Greystone building; a backyard patio is available upon request.
2bd/2bath Urban Loft W/ 2 Pkg Spots 1 Blk To Train - Chicago, IL
9.8 870 reviews
Chicago, IL
25/09 – 30/09
255 €/nighttotal: 1275 € (5 )

2bd/2bath Urban Loft W/ 2 Pkg Spots 1 Blk To Train

1 2
apartment, Chicago
This luxury apartment is located in the Wrigleyville/Lakeview neighbourhood of Chicago, just four blocks from Wrigley Field and one block from the CTA Brown/Red line "el" stop, making it easy to explore the city. The apartment has received excellent ratings for location, cleanliness, and user experience.
The property offers two bedrooms and two bathrooms, comfortably accommodating up to four guests. This stylish apartment comes with a fully equipped kitchen, a large flat-screen TV with cable and Netflix access, a fireplace, two private balconies, a washer and dryer, and free Wi-Fi.
1.5bd|roomy|comfy|roscoe Village Apt Near Wrigley! - Chicago, IL
9.5 46 reviews
Chicago, IL
09/07 – 19/07
185 €/nighttotal: 1850 € (10 )

1.5bd|roomy|comfy|roscoe Village Apt Near Wrigley!

1 3
apartment, Chicago
This Roscoe Village flat is conveniently located 2.1km from Wrigley Field and 14.3km from Chicago's city centre, offering easy access to restaurants, bars, and shops.
The recently remodelled one-bedroom apartment sleeps four guests, boasting a queen bed, full-size daybed with trundle, well-equipped kitchen, private balcony, shared garden, and free on-street parking.
Tree Top 2nd Floor 3 Bedrm Apt - Chicago, IL
9.8 375 reviews
Chicago, IL
28/10 – 05/11
149 €/nighttotal: 1192 € (8 )

Tree Top 2nd Floor 3 Bedrm Apt

3 5
apartment, Chicago
This three-bedroom flat is located just 800 metres from the Blue Line train, providing easy access to downtown Chicago and O'Hare Airport, and sits in a neighbourhood with a variety of bars and restaurants. The apartment has received excellent ratings for its location, cleanliness, and overall experience.
The flat is spacious and comfortably accommodates up to six guests. Amenities include free Wi-Fi, a fully equipped kitchen, a garden, and a sun porch with a view of the backyard, along with free on-street parking and access to a laundry room.
Entire Apartment On The West Loop - Chicago, IL
Chicago, IL
01/07 – 31/07
197 €/nighttotal: 5910 € (30 )

Entire Apartment On The West Loop

2 2
apartment, Chicago
This two-bedroom flat offers immediate proximity to numerous restaurants and nightlife establishments in a prime Chicago district.
This duplex apartment, accommodating up to five guests, boasts a newly renovated kitchen with brand-new appliances, air conditioning, internet access, and exclusive private rooftop access with city views, serviced by Marcia Cleaning Service.
Sunflower Apt 10 Min From Downtown Chicago - Sleeps Up To 6 - Chicago, IL
8.6 21 reviews
Chicago, IL
28/06 – 29/06
250 €/nightfor 1 night

Sunflower Apt 10 Min From Downtown Chicago - Sleeps Up To 6

1 4
apartment, Chicago
This Chicago apartment rental is situated in Brighton Park, a residential neighbourhood on the city's Far South Side, approximately 5 kilometres from Little Italy, Chinatown, and the city centre.
The 60 square metre flat comprises two bedrooms, one bathroom, and sleeps six guests, offering a full kitchen, laundry facilities, two smart TVs, and free high-speed Wi-Fi; nearby attractions include Sox Park and, slightly further afield, Millennium Park and Soldier Field.
Cozy Chic Chicago- Freshly Renovated - Chicago, IL
10 42 reviews
Chicago, IL
19/09 – 05/10
176 €/nighttotal: 2816 € (16 )

Cozy Chic Chicago- Freshly Renovated

1 4
apartment, Chicago
This newly remodelled two-bedroom flat in Chicago offers excellent access to the city's renowned landmarks, with convenient street and designated parking, and a ground-floor coffee and crepe shop.
This second-floor residence accommodates up to four guests, featuring a separate entrance, air conditioning, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher.
Cabin 105 At 747 Lofts - Chicago, IL
9.1 57 reviews
Chicago, IL
02/07 – 05/07
173 €/nighttotal: 519 € (3 )

Cabin 105 At 747 Lofts

1 2
apartment, Chicago
This Chicago studio apartment enjoys an excellent location near the Blue Line 'L' train, providing easy access to the city centre and Randolph Street's restaurants in the West Loop.
The self-contained apartment, sleeping two, features a modern kitchen with fridge, microwave, and dishwasher, in-unit laundry, and a spa bath; parking is not guaranteed, but assistance is provided.
Andersonville Living - Chicago, IL
9.9 477 reviews
Chicago, IL
14/08 – 17/08
245 €/nighttotal: 735 € (3 )

Andersonville Living

1 4
apartment, Chicago
This Andersonville apartment, located off Clark Street in Chicago, offers easy access to the neighbourhood's shops and restaurants.
Sleeping six, this three-bedroom, one-bathroom flat boasts a modern kitchen, basement laundry, free Wi-Fi, cable TV, and Amazon streaming; a garden and parking are also available.

Best family friendly Chicago, IL lodging

Among the 11918 accommodations in Chicago, IL, here are the 4 best for families

Skylights, King Bed, 2 Bedrooms - Chicago, IL
9.8 285 reviews
Chicago, IL
02/10 – 04/10
220 €/nighttotal: 440 € (2 )

Skylights, King Bed, 2 Bedrooms

2 6
apartment, Chicago
This two-bedroom apartment is situated in Irving Park East, just a short distance from the CTA Blue Line and buses, making it easy to explore all that Chicago has to offer. The apartment has received excellent ratings for location, cleanliness and user experience.
The apartment comfortably accommodates up to six guests and comes equipped with a full kitchen, laundry facilities, and a 42-inch flat-screen TV with Roku. Guests can enjoy the convenience of free on-street parking and key code entry for flexible arrival times.
Spacious 3600 Sq Ft. Home Next To Park & Transit - Chicago, IL
9.9 152 reviews
Chicago, IL
27/06 – 04/07
515 €/nighttotal: 3605 € (7 )

Spacious 3600 Sq Ft. Home Next To Park & Transit

1 8
apartment, Chicago
This spacious Chicago apartment, situated in the Irving Park neighbourhood, offers easy access to downtown Chicago (approx. 21km), O'Hare International Airport (approx. 19km), and Wrigley Field (approx. 21km) via the nearby CTA Blue Line.
The 340 sq m property boasts six bedrooms, three bathrooms, sleeping up to 14 guests, and includes amenities such as a garden, parking, high-speed internet, and family-friendly extras like a travel cot and high chair; nearby attractions include a park with playground, gym, and pool.
The Bright Retreat In Andersonville - Chicago, IL
9.4 7 reviews
Chicago, IL
04/07 – 06/07
346 €/nighttotal: 692 € (2 )

The Bright Retreat In Andersonville

1 3
apartment, Chicago
This Andersonville apartment in Chicago is situated near Foster Beach (2.9km) and Montrose Beach (2.3km), also close to Loyola University Chicago (3.2km).
This one-bedroom, one-bathroom flat sleeps seven guests and offers free Wi-Fi, private parking, a fully equipped kitchen, and air conditioning; nearby attractions include Lincoln Park Zoo (8.4km) and Wrigley Field (3.7km).
Foosball, Steps From Wrigley, Private Parking - Chicago, IL
9.8 166 reviews
Chicago, IL
11/07 – 13/07
489 €/nighttotal: 978 € (2 )

Foosball, Steps From Wrigley, Private Parking

1 3
apartment, Chicago
This Chicago apartment rental is ideally situated near Wrigley Field and the Red Line, offering easy access to Chicago's North Side attractions.
The two-bedroom, two-bathroom flat sleeps five guests and includes a fully equipped kitchen, free on-site parking (a rarity in this area), and access to the entire condo.

Best Chicago, IL accommodations with a kitchen

Walk To The Beach And Golf From Our 3 Story Home. - Chicago, IL
9.4 63 reviews
Chicago, IL
08/10 – 15/10
346 €/nighttotal: 2422 € (7 )

Walk To The Beach And Golf From Our 3 Story Home.

1 4
house, Chicago
This spacious Chicago house, ideal for groups, offers four bedrooms and two bathrooms sleeping up to twelve guests, and boasts a 251-square-metre floor area across three floors.
The property includes a fully equipped kitchen, rooftop deck with city views, and convenient access to Chicago's attractions, though precise distances to landmarks are not specified.
Entire Apt. Train. Uchicago 3blks. Parking Avai. - Chicago, IL
10 17 reviews
Chicago, IL
01/07 – 31/08
101 €/nighttotal: 6161 € (61 )

Entire Apt. Train. Uchicago 3blks. Parking Avai.

1 3
apartment, Chicago
This Woodlawn apartment, situated 0.5km from a grocery store and 0.8km from the Green Line, offers convenient access to the University of Chicago Medical Centre, just 0.45km away.
The two-bedroom, two-bathroom dwelling, fully furnished with amenities including a private garden and parking, comfortably sleeps four and features a modern kitchen, in-unit laundry, and a free bike for exploring Hyde Park.
The Atlas Highrise® - Luxury 2br W/ Gym, W+d, Pool - Chicago, IL
10 1 review
Chicago, IL
01/01 – 31/12
14 €/nighttotal: 5096 € (364 )

The Atlas Highrise® - Luxury 2br W/ Gym, W+d, Pool

2 2
apartment, Chicago
This Chicago flat is situated centrally, offering a 5-15 minute walk or drive to Michigan Avenue, Lakeshore, Navy Pier, Millennium Park, and several major beaches.
This two-bedroom, one-bathroom apartment accommodates up to six guests and boasts a fully equipped kitchen, high-speed WiFi, in-unit laundry, and access to building amenities including a seasonal swimming pool, fitness centre, and 24/7 concierge service, with private parking available for an additional fee.
Lake Meadows Chic 1br Getaway - Chicago, IL
9.6 11 reviews
Chicago, IL
24/07 – 27/07
161 €/nighttotal: 483 € (3 )

Lake Meadows Chic 1br Getaway

1 2
apartment, Chicago
This 1-bedroom flat in Lake Meadows, Chicago, is situated in the Lake Meadows district, offering proximity to the lakefront and beach, approximately 1.6 kilometres away.
This fully furnished apartment accommodates two guests and includes a kitchen with a fridge and microwave, with dogs and cats welcome subject to approval.

Frequently asked questions about accommodations in Chicago, IL

  • What are the top attractions and must-see sites in Chicago, IL?

    Chicago is packed with iconic sights! You definitely want to see the Willis Tower (formerly Sears Tower) for incredible city views. The Art Institute of Chicago is a must for any art lover, and you can't miss Millennium Park with its famous Cloud Gate sculpture, nicknamed 'The Bean'. And of course, no trip to Chicago is complete without a stroll along Navy Pier, with its Ferris wheel and bustling atmosphere.
  • What are the best accommodations in Chicago, IL?

  • Which cultural festivals and seasonal events should visitors attend in Chicago, IL?

    Chicago is a city that loves its festivals! In the summer, you'll find the Chicago Blues Festival and the Taste of Chicago, a huge food festival. For something a bit different, check out the Chicago Air and Water Show in August. And in the winter, don't miss the Christkindlmarket, a festive German Christmas market.
  • What are the best accommodations with a pool in Chicago, IL?

  • What are the most convenient modes of transportation within Chicago, IL?

    The Chicago 'L' (elevated train) is the most efficient way to get around. It's easy to navigate and covers most of the city. You can also use the extensive bus network, or try Divvy, the city's bike-sharing system. Taxis and ride-sharing services are also readily available.
  • What are the best accommodations with a jacuzzi in Chicago, IL?

    The best accommodations with a jacuzzi in Chicago, IL are Classy And Cozy 2nd - Room, The Langham Chicago and Park Hyatt Chicago.

  • What outdoor activities and adventures are popular in and around Chicago, IL?

    Chicago has a lot to offer outdoors! Head to Lincoln Park for a walk or bike ride, or explore the scenic Lakefront Trail, which stretches along the lake. For a bit of adventure, try kayaking or stand-up paddleboarding on Lake Michigan. And if you're up for a day trip, visit the Morton Arboretum, a beautiful botanical garden just outside the city.
  • What are the best accommodations for families and kids in Chicago, IL?

    The best accommodations for families and kids in Chicago, IL are Artist Loft - Very Unique, The Peninsula Chicago and Mag Mile Mega Entire Floor 4bd\/4ba+parking&rooftop.

  • What types of accommodations are available in Chicago, IL?

    You'll find everything from budget-friendly hostels to luxurious hotels in Chicago. There are also plenty of charming bed and breakfasts and vacation rentals available. For a unique experience, consider staying in a historic hotel like the Palmer House Hilton or the Congress Plaza Hotel.
  • What are the best pet friendly accommodations in Chicago, IL?

    The best pet friendly accommodations in Chicago, IL are Artist Loft - Very Unique, Art Deco-queen-salle De Bain Partagée and The Peninsula Chicago.

  • When is the best time to visit Chicago, IL?

    Spring and autumn are generally the most pleasant times to visit Chicago, with mild temperatures and fewer crowds. Summer can be hot and humid, but it's a great time for outdoor activities and festivals. Winter can be cold, but it's a magical time to experience the city's festive atmosphere.
  • What are the best accommodations with parking in Chicago, IL?

  • What local dishes and culinary experiences are a must-try in Chicago, IL?

    Chicago is a foodie paradise! You have to try a Chicago-style hot dog, with all the fixings. Deep-dish pizza is a must-try, and don't forget to sample some of the city's famous Italian beef sandwiches. For a sweet treat, grab a slice of Chicago-style cheesecake, or a box of Garrett Popcorn Shops popcorn.
  • In which part of Chicago, IL should you consider renting accommodation?

    The best area to stay depends on your interests. If you want to be close to the action, choose a hotel in the Loop or River North. For a more relaxed atmosphere, consider staying in Lincoln Park or Lakeview. If you're on a budget, the neighborhoods of Wicker Park or Logan Square offer more affordable options.

Destinations nearby

Best Chicago, IL lodgings with a pool

Among the 11918 accommodations in Chicago, IL, here are the 4 best ones with a pool

Fully Furnished Gold Coast Luxury Condo With Sunset View Ideal For 30+ Day Stays - Chicago, IL
Chicago, IL
22/09 – 23/11
119 €/nighttotal: 7378 € (62 )

Fully Furnished Gold Coast Luxury Condo With Sunset View Ideal For 30+ Day Stays

1 2
apartment, Chicago
This luxurious Gold Coast apartment, near the River North border, is steps from Michigan Avenue and Oak Street Beach.
The one-bedroom, one-bathroom flat sleeps two, boasting a fully equipped kitchen, in-unit laundry, high-speed Wi-Fi, a jacuzzi, and access to a building swimming pool, fitness centre, and 24-hour concierge.
Chic Stay In River North: Luxury Suites, Top Amenities, Near Arts & Nightlife! - Chicago, IL
Chicago, IL
04/09 – 05/09
695 €/nightfor 1 night

Chic Stay In River North: Luxury Suites, Top Amenities, Near Arts & Nightlife!

1 4
apartment, Chicago
This Level River North apartment is situated in the River North district of Chicago, minutes from the Magnificent Mile and the Loop, offering easy access to riverside parks.
The 67-square-metre (721-square-foot) one-bedroom flat sleeps four guests and boasts a fully equipped kitchen, including a dishwasher, a terrace, and access to a swimming pool and sauna; nearby water activities include motor boating.
Sentral Premium 2br Apt South Loop Chicago - Chicago, IL
9.4 353 reviews
Chicago, IL
05/09 – 07/09
487 €/nighttotal: 974 € (2 )

Sentral Premium 2br Apt South Loop Chicago

2 3
apartment, Chicago
This apartment is situated in the Grant Park neighbourhood, just a short walk from Millennium Park and the Art Institute of Chicago, offering easy access to the city's cultural highlights. The apartment enjoys excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment features two bedrooms and two bathrooms, comfortably accommodating up to four guests. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, fitness centre, and on-site services such as dry cleaning and a bistro.
The Museum View Villa (Fitness Center • Sauna) - Chicago, IL
9.7 6 reviews
Chicago, IL
21/10 – 20/01
40 €/nighttotal: 3640 € (91 )

The Museum View Villa (Fitness Center • Sauna)

1 2
apartment, Chicago
This Michigan Avenue studio apartment boasts a prime location in Chicago's central area, within walking distance of Millennium Park and Navy Pier, and a short distance from an 'L' train station.
The self-catering apartment sleeps five guests comfortably, featuring a king-size and queen-size bed, a sofa bed, and an air mattress, alongside a fully equipped kitchen, private washer/dryer, and access to a building with extensive amenities including a swimming pool, fitness centre, and sauna.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL accommodations with parking

Cozy Casa By Ohare Airport - Chicago, IL
8.6 31 reviews
Chicago, IL
16/07 – 17/07
126 €/nightfor 1 night

Cozy Casa By Ohare Airport

1 1
apartment, Chicago
This Chicago apartment, conveniently located near O'Hare International Airport (13km from Wrigley Field and 14km from Loyola University Chicago), offers easy access to major attractions.
The one-bedroom flat sleeps up to nine guests, features a fully equipped kitchen, free Wi-Fi, on-site parking, a garden, and air conditioning.
Modern 1br Near Midway - Cta Train - Golf Nearby - Chicago, IL
10 1 review
Chicago, IL
14/08 – 16/08
149 €/nighttotal: 298 € (2 )

Modern 1br Near Midway - Cta Train - Golf Nearby

1 1
apartment, Chicago
This 1-bedroom flat is conveniently located near Midway Airport in Chicago, offering easy access to the CTA train and situated 9 kilometres from Guaranteed Rate Field and 10.1 kilometres from the Museum of Science and Industry.
This property provides 70 square metres of living space with a separate living room, a fully equipped kitchen, and capacity for seven guests, along with free WiFi and air conditioning, while being a non-smoking accommodation suitable for quiet stays.
2br/2ba Long Term Condo In River North - Chicago, IL
10 1 review
Chicago, IL
28/07 – 30/12
117 €/nighttotal: 18135 € (155 )

2br/2ba Long Term Condo In River North

2 2
apartment, Chicago
This furnished two-bedroom, two-bathroom flat is located in Chicago's River North district, offering expansive city views and convenient access to the city's attractions, with the Magnificent Mile approximately 800 meters away.
This apartment boasts a 24-hour doorman, a fitness centre, an in-unit washer and dryer, and bi-weekly cleaning, making it ideal for business or leisure stays for up to two guests.
Welcome To This Four Bedroom, Two Bathroom Apartment Located In The Neighborhood Of Lakeview. - Chicago, IL
Chicago, IL
27/06 – 04/07
784 €/nighttotal: 5488 € (7 )

Welcome To This Four Bedroom, Two Bathroom Apartment Located In The Neighborhood Of Lakeview.

4 3
apartment, Chicago
This four-bedroom flat is located in Chicago's Lakeview district, offering easy access on foot to dining and entertainment along Ashland, Lincoln, and Belmont Avenues, with the Brown Line train station 320 metres away for city exploration.
This property accommodates up to 8 guests with its two bathrooms, open-plan living and kitchen area featuring stainless steel appliances and a breakfast bar, two separate living spaces, and in-unit laundry facilities, with free street parking available.
©2026 cozycozy.com