Search cheap accommodations in Chicago from 100+ sites!

11918 available accommodation offers

7 nights
2
1
  • airbnb
  • booking
  • vrbo
  • expedia
  • sonder
  • priceline
  • tripadvisor
  • tripcom
  • homestay
  • hotelscom
  • orbitz
  • vacasa
Chicago accommodations
Choose the perfect vacation accommodation
Price per night
Accommodation type
Rating

11918 Lodgings in Chicago

Browse Family Lodgings in Chicago

Getting the lodging right makes all the difference for a family trip to Chicago, with city attractions within easy reach at every selected option.

Cozy, Sunny, And Clean Apt 3 Bd Free Parking - Chicago
9.8 70 reviews
Chicago
06/19 – 06/21
$596/nighttotal: $1192 (2 )

Cozy, Sunny, And Clean Apt 3 Bd Free Parking

1 1
apartment , Berwyn
This Berwyn apartment rental boasts a prime location, just 25 minutes from Downtown Chicago and 20 minutes from Midway International Airport, offering easy access via public transportation and major highways.
The three-bedroom, one-bathroom unit comfortably sleeps six guests and features a fully equipped kitchen with dishwasher, in-unit laundry (small fee applies), a shared backyard, and 50-inch TVs in each bedroom plus a 58-inch Smart TV in the living room with Netflix and Disney+.
Modern 3br King Chicago Stay Near United Center - Chicago
Chicago
07/12 – 07/17
$316/nighttotal: $1580 (5 )

Modern 3br King Chicago Stay Near United Center

3 2
apartment , Chicago
This Chicago apartment is located 3.4 miles from the United Center and offers convenient access to attractions such as Union Station (4.9 miles) and the Chicago Museum of Contemporary Art (5 miles).
This 1400 sq ft residence accommodates up to 15 guests, featuring one bedroom, two bathrooms, a full kitchen with a dishwasher and microwave, air conditioning, complimentary Wi-Fi, and free private parking.
Jacuzzi|movie Theater|games|arcade|gym|kid's Space - Chicago
9.5 26 reviews
Chicago
07/31 – 08/03
$1575/nighttotal: $4725 (3 )

Jacuzzi|movie Theater|games|arcade|gym|kid's Space

1 11
apartment , Chicago
This Portage Park district dwelling offers convenient access to Chicago's dining scene, with Trattoria Porretta Ristorante Pizzeria just 322 feet away, and downtown landmarks like Millennium Park and Skydeck Chicago approximately 8-10 miles distant.
This 2,200 sq ft luxury apartment accommodates up to 16 guests with 5 bedrooms and 3 bathrooms, featuring a unique entertainment basement complete with a home theater, arcade machine, game table, popcorn machine, climbing games, a small gym, and an outdoor grass backyard.
Caza Bonita | 3 Level Home | Gated | Parking - Chicago
9.5 91 reviews
Chicago
09/11 – 09/13
$754/nighttotal: $1508 (2 )

Caza Bonita | 3 Level Home | Gated | Parking

1 11
apartment , Chicago
This three-level house in Chicago's North Lawndale neighborhood, undergoing revitalization, offers easy access to downtown Chicago and ethnic enclaves like Pilsen, Little Italy, and Chinatown, with public transportation (bus and Pink Line) two blocks away.
This spacious 4-bedroom, 3-bathroom home sleeps 12, features a fully equipped kitchen, finished basement with game room and laundry, a gated backyard with grill, and includes a baby/child package; private parking accommodates three cars.

Best Chicago accommodation with a kitchen

Pilsen Chicago 6br Getaway With Game Room, Gym & Paid Parking Near Soldier Field & Mccormick Place - Chicago
10 1 review
Chicago
06/19 – 06/21
$1266/nighttotal: $2532 (2 )

Pilsen Chicago 6br Getaway With Game Room, Gym & Paid Parking Near Soldier Field & Mccormick Place

6 4
apartment , Chicago
This 6-bedroom Pilsen apartment is located 2.4 miles from Union Station, 2.5 miles from the United Center, and 2.6 miles from Willis Tower.
This spacious rental offers 110 square feet of living space, accommodates up to 27 guests with its 6 bedrooms and 6 bathrooms, and features a fully equipped kitchen, a garden, a fitness center, and private parking.
Pilsen Art Center Family Friendly 3br Retreat With Free Parking Near Medical District, Douglas Park And University Illinois Chicago - Chicago
10 1 review
Chicago
07/05 – 07/11
$294/nighttotal: $1764 (6 )

Pilsen Art Center Family Friendly 3br Retreat With Free Parking Near Medical District, Douglas Park And University Illinois Chicago

3 8
apartment , Chicago
This three-bedroom Pilsen apartment is located two miles from the United Center and within a 4.5-mile radius of Union Station, the CIBC Theatre, and Grant Park.
This 1500-square-foot family-friendly rental boasts two bathrooms, a fully equipped kitchen, free parking, Wi-Fi, and a balcony, comfortably accommodating up to fifteen guests.
Modern + Cozy Garden Apt W/garage Parking, 20m Dt - Chicago
9.6 31 reviews
Chicago
06/27 – 07/05
$192/nighttotal: $1536 (8 )

Modern + Cozy Garden Apt W/garage Parking, 20m Dt

1 4
apartment , Chicago
This Logan Square apartment rental is located two blocks from the 606 Trail and offers easy access to public transportation, including the Metra and CTA, for convenient travel throughout Chicago.
This two-bedroom, one-bathroom unit sleeps five guests and features a fully equipped kitchen with stainless steel appliances, in-unit laundry, a dedicated office nook, and private garage parking—a rare find in Chicago.
Iklektik House Chicago / Bluejay - Chicago
9.8 244 reviews
Chicago
07/22 – 07/25
$252/nighttotal: $756 (3 )

Iklektik House Chicago / Bluejay

1 2
apartment , Chicago
This West Town Chicago apartment boasts a prime location near the United Center and offers easy access to the Metra Western Avenue and Hubbard lines.
The unit features a king-size bed, a fully equipped kitchen with dishwasher, a clawfoot tub, private keyless entry, and access to a shared backyard with grill; it sleeps two guests and includes free street parking directly in front of the building.

Frequently Asked Questions about accommodations in Chicago

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

    Chicago is full of iconic landmarks. You can't miss the Willis Tower, formerly known as the Sears Tower, for breathtaking views of the city. The Art Institute of Chicago is a must for art lovers, with works by Monet, Picasso, and Van Gogh. And don't forget to walk along Navy Pier, with its Ferris wheel, shops, and restaurants.
  • What are the best accommodations in Chicago?

  • What's the best district to book lodging in Chicago?

    When it comes to booking lodging in Chicago, the best district would be the Magnificent Mile. It offers a wide range of accommodations, from luxury hotels to budget-friendly options, and is conveniently located near popular attractions.
  • Which cultural festivals and seasonal events should visitors attend in Chicago, IL?

    Chicago has festivals throughout the year. In the summer, you'll find the Taste of Chicago, a huge food festival, and Lollapalooza, a four-day music festival. In the fall, the Chicago Marathon brings the city to life. And during the winter, the Christkindlmarket is a charming Christmas market with German food and crafts.
  • What are the best accommodations with a pool in Chicago?

  • Are there any budget-friendly day trips from Chicago?

    There are several budget-friendly day trips from Chicago, such as visiting the Indiana Dunes National Park or exploring the charming town of Galena.
  • What are the most convenient modes of transportation within Chicago, IL?

    The Chicago Transit Authority (CTA) is the best way to get around. You can use the 'L' train, which runs above ground, or the subway, which runs underground. There's also a great bus system. If you're feeling adventurous, try Divvy, the city's bike-sharing program.
  • What are the best accommodations with a jacuzzi in Chicago?

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

  • Which restaurants in Chicago are suitable for business meetings and corporate dinners?

    For a professional setting, The Capital Grille in the Loop offers an upscale dining experience with private rooms. RPM Steak in River North is another excellent choice, known for its refined ambiance and top-notch service, ideal for impressing clients.
  • What outdoor activities and adventures are popular in and around Chicago, IL?

    Chicago has a lot to offer outdoors. You can walk or bike the Lakefront Trail along Lake Michigan. Lincoln Park Zoo is free and a great place to spend a day. Or head to Millennium Park, where you can see the Cloud Gate sculpture, affectionately known as 'The Bean'.
  • What are the best accommodations for families and kids in Chicago?

    The best accommodations for families and kids in Chicago are Artist Loft - Very Unique, The Langham Chicago and The Peninsula Chicago.

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

    Chicago has a wide range of accommodations, from budget-friendly hostels to luxury hotels. You can find everything from boutique hotels in the trendy Wicker Park neighborhood to historic hotels in the Loop, the city's downtown area.
  • What are the best pet friendly accommodations in Chicago?

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

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

    The best time to visit Chicago is in the spring or fall. The weather is mild, and the city is less crowded than in the summer. If you're a fan of winter activities, you can visit during the winter months, but be prepared for cold temperatures.
  • What are the best accommodations with parking in Chicago?

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

    Chicago is known for its deep-dish pizza, which is a must-try. You can also find great Italian beef sandwiches, hot dogs, and Polish sausage. And don't forget to try a Chicago-style hot dog, with all the fixings.
  • In which part of Chicago, IL should you consider renting accommodation?

    It depends on your interests. If you want to be in the heart of the action, stay in the Loop. For a more residential feel, consider the Gold Coast or Lincoln Park. If you're looking for a trendy vibe, check out Wicker Park or Bucktown.

Destinations nearby

Best Chicago lodging with a pool

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

Mod West Loop 2br W/ Gym, Pool, W/d, Nr. Fulton Market, By Blueground - Chicago
Chicago
08/01 – 10/31
$304/nighttotal: $27664 (91 )

Mod West Loop 2br W/ Gym, Pool, W/d, Nr. Fulton Market, By Blueground

2 1
apartment , Chicago
This two-bedroom apartment is located in the West Loop, a trendy neighborhood with restaurants, bars, and shops, within a 5-10 minute walk from Union Station and a short distance from the Chicago French Market. This apartment offers a convenient location for exploring Chicago's vibrant downtown area.
The apartment features a spacious 990 square foot layout, comfortably accommodating up to four guests. Enjoy a fully equipped kitchen, a modern living room, and a private balcony, along with access to building amenities like a gym, swimming pool, and BBQ area.
Blueground | The Loop, Pool & W/d, Nr Park - Chicago
Chicago
08/01 – 06/30
$121/nighttotal: $40293 (333 )

Blueground | The Loop, Pool & W/d, Nr Park

1 1
apartment , Chicago
This one-bedroom Chicago Loop apartment offers prime access to Millennium Park, Grant Park, the Art Institute of Chicago, and Soldier Field, all within walking distance.
The 650-square-foot unit sleeps two guests and includes in-unit laundry, a fully equipped kitchen with dishwasher, and building amenities such as a swimming pool and BBQ area.
Ideal Streeterville Studio W/ Gym, Pool, Walk To Navy Pier, By Blueground - Chicago
10 1 review
Chicago
08/01 – 06/30
$110/nighttotal: $36630 (333 )

Ideal Streeterville Studio W/ Gym, Pool, Walk To Navy Pier, By Blueground

1 1
studio , Chicago
This Streeterville studio, a Blueground apartment, offers stunning city views in Chicago's central Streeterville neighborhood, close to Lake Michigan and numerous attractions.
The 590-square-foot unit features one bedroom, one bathroom, accommodates two guests, and includes amenities such as a swimming pool, fitness center, parking (fee applies), and in-building laundry.
South Loop Rooftop With In And Out Parking 2 - Chicago
9.8 4 reviews
Chicago
08/13 – 08/17
$767/nighttotal: $3068 (4 )

South Loop Rooftop With In And Out Parking 2

2 2
apartment , Chicago
This South Loop Chicago apartment boasts prime proximity to Willis Tower (a 10-minute walk), the Chicago Symphony Orchestra (a 14-minute walk), and Union Station (0.7 miles).
This 880-square-foot rental features two bedrooms, two bathrooms, accommodates seven guests, and includes a fully equipped kitchen, in-unit laundry, free Wi-Fi, access to a fitness center and swimming pool, and convenient access to nearby cycling routes and attractions like Grant Park and the Art Institute of Chicago.

Neighborhoods and points of interest in Chicago

Best Chicago accommodation with parking

Updated Home With Vintage Charm - Chicago
10 35 reviews
Chicago
07/05 – 07/10
$346/nighttotal: $1730 (5 )

Updated Home With Vintage Charm

1 5
apartment , Chicago
This Uptown Chicago apartment rental is located two blocks from the Aragon Ballroom, Riviera Theatre, and Green Mill Cocktail Lounge, and a 15-minute walk from Lake Michigan, with easy access to the CTA Red Line.
This four-bedroom, 1.5-bathroom unit sleeps eight guests and features a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, plus in-unit laundry, parking, and air conditioning; enjoy nearby Uptown attractions and easy access to Wrigley Field and downtown.
City Villa Sleeps 10-20 Free Tv & Parking - Chicago
9.4 20 reviews
Chicago
06/21 – 06/23
$505/nighttotal: $1010 (2 )

City Villa Sleeps 10-20 Free Tv & Parking

4 4
apartment , Chicago
This Chicago apartment is located in the Lakeview neighborhood, just a short walk from Wrigley Field and within easy reach of popular attractions like Fullerton Beach, 360 Chicago, and Water Tower Chicago. It consistently receives excellent ratings for its location, cleanliness, and overall experience.
This spacious 4-bedroom, 2-bathroom rental can comfortably accommodate 10-20 guests, making it perfect for large families or groups. Guests can enjoy a fully equipped kitchen, a relaxing terrace with city views, on-site parking, and access to a variety of activities in and around Chicago.
Bridgeport Place -Free Parking, Mccormick-sox Park - Chicago
9.8 7 reviews
Chicago
07/17 – 07/21
$400/nighttotal: $1600 (4 )

Bridgeport Place -Free Parking, Mccormick-sox Park

1 1
apartment , Chicago
This pet-friendly apartment in Chicago's Bridgeport neighborhood is just a short drive from Guaranteed Rate Field and State Street, making it a convenient base for exploring the city. The area is known for its lively atmosphere and proximity to various attractions.
This one-bedroom apartment comfortably accommodates up to four guests and features a fully equipped kitchen, a private patio, and a washer and dryer. Guests can enjoy amenities like free Wi-Fi, air conditioning, and a desk, along with nearby access to the Chicago River for kayaking and exploring the city's waterfront.
Mccormick Oasis With Balcony, Optional Parking, Patio And Gym Sleeps 6 Near Mccormick Place, Grant Park, Soldier Field & Museum Campus - Chicago
8.3 4 reviews
Chicago
07/15 – 07/18
$409/nighttotal: $1227 (3 )

Mccormick Oasis With Balcony, Optional Parking, Patio And Gym Sleeps 6 Near Mccormick Place, Grant Park, Soldier Field & Museum Campus

2 6
apartment , Chicago
This apartment is located in Chicago, just 1.5 miles from the Field Museum and within walking distance of the Art Institute of Chicago and the Chicago Symphony Orchestra. The surrounding area offers easy access to public transportation and a variety of dining and entertainment options.
This 2-bedroom rental is perfect for families or groups of up to 6 guests. It has 900 square feet of space and includes amenities like a fully equipped kitchen, a private balcony, a fitness center, and parking.
©2026 cozycozy.com