Places to stay in Chicago, IL

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Chicago, IL place to stay
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11918 Best places to stay in Chicago, IL

Best family friendly Chicago, IL lodging

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

Grade A Working Class Safe Neighborhood 3br Up To 6 Guests. Updated & Best Price - Chicago, IL
10 3 reviews
Chicago, IL
19/08 – 18/12
SG$263/nighttotal: SG$31823 (121 )

Grade A Working Class Safe Neighborhood 3br Up To 6 Guests. Updated & Best Price

3 2
apartment , Burbank
This three-bedroom Burbank apartment, near Chicago Midway International Airport and a 40km drive from downtown Chicago, offers convenient access to major attractions including Grant Park and Millennium Park.
Sleeping six guests, this self-catering property boasts a full kitchen with dishwasher, a washer/dryer, free Wi-Fi, a smart TV, on-site parking, and three Ring security cameras; nearby amenities include restaurants, grocery stores, parks, and a water park.
Animal House Near Sox Stadium - Chicago, IL
8.6 16 reviews
Chicago, IL
12/09 – 17/09
SG$210/nighttotal: SG$1050 (5 )

Animal House Near Sox Stadium

1 2
apartment , Chicago
This Bridgeport, Chicago flat is conveniently located near the Field Museum and Art Institute of Chicago.
The 111-square-metre (1194 square feet) apartment sleeps four, boasting a kitchen with fridge, microwave, and dishwasher, plus a spa, air conditioning, and pet-friendly amenities including a dog run and even a 'loaner' pet.
2 Bdrm Quiet Berwyn Apt W/ Free Garage - Chicago, IL
9.8 66 reviews
Chicago, IL
27/06 – 05/07
SG$275/nighttotal: SG$2200 (8 )

2 Bdrm Quiet Berwyn Apt W/ Free Garage

1 4
apartment , Berwyn
This Berwyn apartment, situated 22.5 kilometres from downtown Chicago, offers easy access to attractions such as Navy Pier, Millennium Park, and the Willis Tower.
The two-bedroom, one-bathroom flat sleeps six guests and features a fully equipped kitchen, in-building laundry facilities, guaranteed garage parking, and a shared patio; the entire second floor provides complete privacy.
The Urban Oasis | Outdoor Lounge • Sleeps 10+ - Chicago, IL
9.9 164 reviews
Chicago, IL
02/07 – 06/07
SG$1185/nighttotal: SG$4740 (4 )

The Urban Oasis | Outdoor Lounge • Sleeps 10+

1 10
apartment , Chicago
This modern four-bedroom apartment in Pilsen is a 5-minute drive from downtown Chicago, close to attractions like Millennium Park and the United Center, and within easy walking distance of Chinatown and Little Italy. The apartment has received excellent ratings for location, cleanliness and overall experience.
The spacious home is ideal for large groups of up to 12 guests, with two bathrooms and a fully equipped kitchen. The apartment has a garden, free on-street parking, and amenities such as air conditioning, laundry facilities, and high-speed internet.

Best Chicago, IL accommodations with a kitchen

Entire 3br 2 Bath Apartment Near By Northwestern Univ And Transport 8+ Guests - Chicago, IL
Chicago, IL
18/06 – 19/06
SG$587/nightfor 1 night

Entire 3br 2 Bath Apartment Near By Northwestern Univ And Transport 8+ Guests

3 8
apartment , Evanston
This South Evanston flat offers convenient walking access to eateries and public transport, with Evanston Beach and Northwestern University a short drive away.
This three-bedroom, two-bathroom property accommodates up to nine guests and includes a microwave, dishwasher, and air conditioning, serving as a comfortable base for exploring Chicago's attractions.
Lovely Near Loyola - Enjoy The Wonderful Outdoor Space And Sun Room - Room For The Whole Crew Apts - Chicago, IL
9.8 326 reviews
Chicago, IL
21/07 – 26/07
SG$649/nighttotal: SG$3245 (5 )

Lovely Near Loyola - Enjoy The Wonderful Outdoor Space And Sun Room - Room For The Whole Crew Apts

3 4
apartment , Chicago
This three-bedroom flat is conveniently located just a few blocks from Loyola University in Chicago, within easy walking distance of Lake Michigan and a wide range of restaurants. The property has consistently received excellent ratings for its cleanliness, location and overall guest experience.
The flat is fully furnished and sleeps up to seven guests, with a queen bed, two double beds and a pull-out futon. Amenities include a fully equipped kitchen, a sunroom with a backyard, three televisions, Wi-Fi, cable TV and a parking permit for one car.
Cozy Retreat In Hyde Park With In Unit Laundry - Chicago, IL
Chicago, IL
20/06 – 18/07
SG$439/nighttotal: SG$12292 (28 )

Cozy Retreat In Hyde Park With In Unit Laundry

1 1
apartment , Chicago
This Hyde Park flat offers proximity to the University of Chicago and the Museum of Science and Industry, with Lake Michigan just a short walk away.
This 46 square metre studio apartment accommodates two guests and features a fully equipped kitchen, air conditioning, and Wi-Fi, with parking available via apps.
Skyline 2br In South Loop Chicago Near Mccormick - Chicago, IL
9.7 147 reviews
Chicago, IL
29/06 – 03/07
SG$336/nighttotal: SG$1344 (4 )

Skyline 2br In South Loop Chicago Near Mccormick

1 2
apartment , Chicago
This Michigan Avenue apartment offers a prime location near McCormick Place, within walking distance of public transport and Grant Park.
The two-bedroom, two-bathroom flat sleeps six guests comfortably, boasting a fully equipped kitchen, in-building gym, and 4K smart HDTV; optional parking is available at £24 per day.

Frequently asked questions about accommodations in Chicago, IL

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

    Chicago's got a ton of iconic spots! You can't miss the Willis Tower (formerly Sears Tower) for incredible views, Millennium Park with its Cloud Gate sculpture, and Navy Pier for its Ferris wheel and entertainment. And of course, you need to walk along the Magnificent Mile, a stretch of shops and restaurants. You'll find plenty of museums too, like the Art Institute of Chicago and the Field Museum.
  • What are the best accommodations in Chicago, IL?

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

    Chicago's got something going on all year round! In the summer, there's the Taste of Chicago, a huge food festival, and Lollapalooza, a massive music festival. For the holidays, you've got the Christkindlmarket, a German Christmas market, and the ZooLights at Lincoln Park Zoo. And don't forget about the Chicago Marathon in the autumn!
  • What are the best accommodations with a pool in Chicago, IL?

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

    Chicago's got a great public transport system! The 'L' (elevated train) is super convenient for getting around the city centre, and the buses cover a wide range of areas. If you're feeling adventurous, try the water taxis on the Chicago River. And of course, you can always rent a Divvy bike for a more active way to explore.
  • 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's got plenty of outdoor fun! You can walk or bike the Lakefront Trail along Lake Michigan, visit Lincoln Park Zoo, or take a boat tour on the Chicago River. If you're up for a longer trip, head out to Indiana Dunes National Park, just a short drive away, for some beautiful beaches and hiking trails.
  • 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 2bd/2ba Mag Mile Masterpiece (+Rooftop).

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

    You'll find a wide range of accommodation in Chicago, from budget-friendly hostels to luxurious hotels. You've got everything from trendy boutique hotels in the trendy Wicker Park neighbourhood to classic hotels in the Loop. And of course, there are plenty of Airbnb options for a more local feel.
  • 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?

    Chicago is beautiful all year round, but it really depends on what you're looking for. Spring and autumn are mild and pleasant, perfect for exploring the city. Summer is great for festivals and outdoor activities, but can get hot and humid. Winter is cold and snowy, but you can enjoy holiday markets and ice skating.
  • What are the best accommodations with parking in Chicago, IL?

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

    Chicago's food scene is amazing! You have to try a Chicago-style hot dog with all the fixings, and a deep-dish pizza. And don't forget to grab a Chicago-style Italian beef sandwich. There's also a great craft beer scene, with loads of breweries to explore.
  • In which part of Chicago, IL should you consider renting accommodation?

    It really depends on what you're looking for! If you want to be in the heart of the action, the Loop is a great choice. For a more trendy vibe, check out Wicker Park or River North. If you're on a budget, you can find good deals in neighborhoods like Pilsen or Logan Square. And for a quieter experience, try Lincoln Park or Lakeview.

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

Blueground | Streeterville, Pool & Gym, Nr Pier - Chicago, IL
Chicago, IL
01/08 – 30/06
SG$136/nighttotal: SG$45288 (333 )

Blueground | Streeterville, Pool & Gym, Nr Pier

1 1
apartment , Chicago
This Streeterville flat is ideally located a short walk (0.8km) from Chicago's Loop, offering easy access to Navy Pier and Michigan Avenue.
The 60 square metre apartment features one bedroom, one bathroom, sleeps two guests, and includes a fully equipped kitchen, swimming pool access, and high-floor city views.
Blueground | Little Italy, Pool, Nr Uic - Chicago, IL
Chicago, IL
01/08 – 30/06
SG$138/nighttotal: SG$45954 (333 )

Blueground | Little Italy, Pool, Nr Uic

1 1
apartment , Chicago
This one-bedroom flat is located in Chicago's Little Italy district, offering convenient access to local attractions.
This thoughtfully furnished apartment accommodates two guests and features a fully equipped kitchen, a swimming pool, a fitness centre, and in-building laundry, with pets welcome subject to restrictions.
Level Chicago - Old Town - Chicago, IL
9.2 1473 reviews
Chicago, IL
19/08 – 24/08
SG$416/nighttotal: SG$2080 (5 )

Level Chicago - Old Town

1 2
hotel , Chicago
Level Chicago - Old Town is situated in the trendy Old Town neighbourhood, a short walk from Oak Street and North Avenue beaches and known for its historic architecture and lively nightlife. The hotel has excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The hotel offers a range of accommodation options, including rooms with balconies. Guests have access to a swimming pool, fitness centre, spa, sauna, hot tub, shared kitchen, terrace, lounge, ping pong and darts, a business centre, and a restaurant.
Stay Wavy - Chicago, IL
Chicago, IL
20/06 – 22/08
SG$260/nighttotal: SG$16380 (63 )

Stay Wavy

1 2
apartment , Chicago
This luxurious Chicago apartment, situated on the 12th floor of a secure building, offers panoramic city views and its precise location within the city will be disclosed upon booking.
The 1-bedroom, 1-bathroom flat boasts a spacious open-plan layout, sleeping up to 2 guests, and includes amenities such as a swimming pool, fitness centre, and air conditioning.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL accommodations with parking

River North Private Deck With In And Out Parking - Chicago, IL
9.6 9 reviews
Chicago, IL
25/06 – 26/06
SG$1152/nightfor 1 night

River North Private Deck With In And Out Parking

3 5
apartment , Chicago
This spacious Chicago city centre flat is ideally located within walking distance of the Chicago Theatre and Art Institute, a short drive from Millennium Park and Navy Pier.
The 151 square metre three-bedroom property sleeps nine guests, boasting a private balcony, free parking nearby, and access to building amenities including a rooftop terrace, gym, and streaming services; a portable cot is also available.
Relaxing In Ravenswood - This Neighborhood Is Great For Any Group And Close To Everything! By Allset Turnover - Chicago, IL
9.7 310 reviews
Chicago, IL
21/09 – 24/09
SG$289/nighttotal: SG$867 (3 )

Relaxing In Ravenswood - This Neighborhood Is Great For Any Group And Close To Everything! By Allset Turnover

2 2
apartment , Chicago
This two-bedroom flat is situated in Ravenswood, a lively northside neighbourhood in Chicago, just a short journey from the city centre by public transport. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The flat comfortably accommodates up to five guests, making it ideal for families or groups of friends. The well-equipped kitchen, along with the laundry facilities and other amenities, offer everything you need for a relaxing and stress-free stay.
Sleeps7 • 2br • Coffee Station • Backyard W/ Grill - Chicago, IL
Chicago, IL
25/06 – 26/06
SG$675/nightfor 1 night

Sleeps7 • 2br • Coffee Station • Backyard W/ Grill

2 1
apartment , Chicago
This Chicago detached house is located approximately 12 kilometres from the United Centre and 12.2 kilometres from Lincoln Park Zoo, offering straightforward access to several key city attractions.
This detached house provides accommodation for up to 7 guests across 2 bedrooms, featuring a fully equipped kitchen with an oven and microwave, complimentary WiFi, and a backyard with a grill, all within a 1000 square metre floor area.
Modern, 2-bedroom Apt., 15 Minute Drive To Lake Michigan, Free Parking Spot. - Chicago, IL
9.2 24 reviews
Chicago, IL
13/08 – 17/08
SG$288/nighttotal: SG$1152 (4 )

Modern, 2-bedroom Apt., 15 Minute Drive To Lake Michigan, Free Parking Spot.

2 2
apartment , Chicago
This two-bedroom Chicago apartment rental is situated in the West Ridge neighbourhood, offering convenient access to Lake Michigan and Millennium Park, although precise distances aren't specified.
The family-friendly flat, sleeping four, includes a fully equipped kitchen, designated workspace with high-speed internet, private parking, and on-site host support; nearby attractions include the Field Museum and Wrigley Field.
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