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Best Short term and Weekly rentals in Chicago

Wrigleyville Flat - Bright Spacious 3br/1bath - Chicago
9.9 80 reviews
Chicago
5 3
$874/nighttotal: $2622 (3 )

Wrigleyville Flat - Bright Spacious 3br/1bath

apartment - Chicago
This private 2nd-floor apartment is situated in Chicago, just three blocks from Wrigley Field and conveniently close to the Addison Red Line and Southport Brown Line stations.
This 3-bedroom unit accommodates up to 6 guests and features a kitchen with a fridge, microwave, and dishwasher, air conditioning, a sunroom/office, and a backyard oasis with a fire pit and picnic table.
Modern Completely Remodeled Bright, Spacious Flat Steps From Wrigley Field &Bars - Chicago
9.6 25 reviews
Chicago
2 2
$225/nighttotal: $13500 (60 )

Modern Completely Remodeled Bright, Spacious Flat Steps From Wrigley Field &Bars

apartment - Chicago
This Lakeview condo is located less than a mile from Wrigley Field, Lake Michigan, and the Vic Theatre, offering easy access to the Red Line's Addison and Belmont stations.
The 1,070-square-foot apartment features two bedrooms, two bathrooms, accommodates six guests, and includes a patio, fireplace, free Wi-Fi, and a fully equipped kitchen.
1br Retreat: Roomy & Well-appointed - Chicago
9.3 8 reviews
Chicago
2 1
$149/nighttotal: $447 (3 )

1br Retreat: Roomy & Well-appointed

apartment - Chicago
This 1-bedroom, 1-bathroom condo in Chicago is conveniently located near local restaurants and shops, offering easy access to neighborhood exploration.
This pet-friendly unit features a fully equipped kitchen with a fridge and microwave, a king-sized bed, a dedicated workspace, and reliable WiFi, accommodating up to 2 guests.
The Richmond Attic | Cool Artsy Suite Next To 606 - Chicago
10 1 review
Chicago
1 1
$144/nighttotal: $12960 (90 )

The Richmond Attic | Cool Artsy Suite Next To 606

apartment - Chicago
This top-floor, one-bedroom condo in a quiet residential building offers immediate access to Chicago's attractions, perfect for digital nomads and traveling professionals.
This apartment features a full kitchen with essential appliances, air conditioning, and a fitness center, ideal for long-term stays with a capacity of four guests and two beds.
Chic Retreat Near The Best Of Lakeview & Wrigley - Chicago
9.9 184 reviews
Chicago
2 1
$271/nighttotal: $542 (2 )

Chic Retreat Near The Best Of Lakeview & Wrigley

apartment - Chicago
This Chicago apartment is located in the trendy Southport Corridor neighborhood, just blocks from shopping, dining, and Wrigley Field. It has excellent user, location, and cleanliness ratings. This one-bedroom rental sleeps two guests and is perfect for a couple or solo traveler. The apartment features a spacious layout, a well-equipped kitchenette, a spa-like bathroom, and a Peloton exercise bike.
Guest Favorite | Private Entrance | Free Parking - Chicago
9.8 113 reviews
Chicago
2 2
$256/nighttotal: $1792 (7 )

Guest Favorite | Private Entrance | Free Parking

apartment - Chicago
This Chicago apartment rental (R23000115681) offers a 2-bedroom, 1-bathroom unit sleeping four, with convenient access to [Specific Chicago neighborhood and proximity to landmarks, e.g., "the Magnificent Mile, within walking distance of Millennium Park"].
The apartment includes a fully equipped kitchen with fridge, freezer, microwave, and dishwasher; air conditioning, parking, and late checkout (fee applies) are also available.
Cozy 2bd/1ba In Charming Logan Square - Chicago
9.4 207 reviews
Chicago
3 2
$106/nighttotal: $1272 (12 )

Cozy 2bd/1ba In Charming Logan Square

apartment - Chicago
This Logan Square garden unit offers easy access to downtown Chicago via the nearby Logan Square Blue Line L station.
The 2-bedroom, 1-bathroom apartment sleeps 5, features a private patio, electric fireplace, and includes parking; pet-friendly with a $150 cleaning fee.
Spacious & Serene In Hip Spot. Sleeps 4. - Chicago
9.8 527 reviews
Chicago
2 1
$83/nighttotal: $166 (2 )

Spacious & Serene In Hip Spot. Sleeps 4.

apartment - Chicago
This Pilsen guesthouse is conveniently located near Thalia Hall, the National Museum of Mexican Art, and the 18th Street Pink Line station, offering easy access to downtown Chicago.
The 2,500-square-foot home features one bedroom with a queen-size bed, a shared bathroom with a jacuzzi tub, and can accommodate up to four guests with an additional queen-size air mattress; amenities include a full kitchen, free parking (seasonal, permit required), and laundry facilities.
Spectacular Pilsen Studio For 2! - Chicago
9.8 327 reviews
Chicago
2 1
$111/nighttotal: $666 (6 )

Spectacular Pilsen Studio For 2!

apartment - Chicago
This studio apartment in Pilsen is a short walk from Thalia Hall and a quick drive to the Loop, placing you in the heart of Chicago's vibrant cultural scene. Guests consistently rate this apartment excellent for location, cleanliness, and overall experience.
The studio apartment comfortably accommodates two guests and is equipped with modern amenities for a pleasant stay. Enjoy a fully equipped kitchen, free Wi-Fi, air conditioning, and parking options, ensuring a comfortable and convenient experience.
Great Location Studio In The Gold Coast!! - Chicago
9.8 520 reviews
Chicago
2 1
$155/nighttotal: $310 (2 )

Great Location Studio In The Gold Coast!!

apartment - Chicago
This Gold Coast studio is a prime option for travelers seeking a central and well-rated accommodation in Chicago. Located in the heart of this upscale neighborhood, it offers easy access to Oak Beach, the Magnificent Mile, and the John Hancock Tower, all within a 5-minute walk.
The studio features a compact and cozy layout, ideal for solo travelers or couples. It includes a refrigerator, microwave, and coffee maker, as well as access to on-site laundry facilities. With excellent user, location, and cleanliness ratings, this studio provides a comfortable and convenient base for exploring Chicago's attractions and amenities.
3br Near O'hare • Office • Coffee Bar • Sleeps 9 - Chicago
Chicago
6 3
$449/nightfor 1 night

3br Near O'hare • Office • Coffee Bar • Sleeps 9

apartment - Chicago
This 3-bedroom rental unit is located in Chicago, 3.7 miles from O'Hare International Airport, with Wrigley Field 11 miles away.
This 1050 square foot residence offers accommodation for up to 17 guests, featuring a fully equipped kitchen, free WiFi, air conditioning, and in-unit laundry.
Spacious 5 Br / King Beds / Private Deck + Parking - Chicago
10 98 reviews
Chicago
10 5
$790/nighttotal: $2370 (3 )

Spacious 5 Br / King Beds / Private Deck + Parking

apartment - Chicago
This Chicago house rental, near Garfield Park, is 0.5 miles from the Green Line CTA station, offering easy access to downtown and is 1.4 miles from the Garfield Park Conservatory.
This five-bedroom, two-bathroom home sleeps twelve guests and features a fully equipped kitchen, high-speed internet (600+ Mbps), a private patio with a tiki bar, on-site axe throwing, and two private parking spaces.

Discover Central Short-Term Rentals in Chicago

Experience vibrant local dining and nightlife by reserving central short-term rentals placed inside the heart of Chicago.

Exclusive High-rise In Chicago - Chicago
9.7 6 reviews
Chicago
3 1
$124/nighttotal: $12772 (103 )

Exclusive High-rise In Chicago

apartment - Chicago
This downtown Chicago apartment rental boasts stunning west-facing views of the Chicago River and Lake Michigan, steps from the city's major attractions and public transportation.
The one-bedroom, one-bathroom unit sleeps three guests and includes in-unit laundry, a fully equipped kitchen, and access to a building with a fitness center, swimming pool, jacuzzi, and parking (additional $350/month).
30 E. Huron #3201 Private Residence - Chicago
10 1 review
Chicago
2 1
$124/nighttotal: $7440 (60 )

30 E. Huron #3201 Private Residence

apartment - Chicago
This fully furnished 1-bedroom, 1-bathroom condo in a quiet Chicago residential high-rise offers a convenient base for exploring the city, with easy access to its attractions.
This pet-friendly apartment features a modern kitchen with stainless steel appliances, a king-size bed, and access to building amenities including a swimming pool and fitness center, accommodating up to 3 guests.
Kasa | Elevate Your Stay, Premium Studio | Chicago - Chicago
9.5 64 reviews
Chicago
2 1
$161/nighttotal: $644 (4 )

Kasa | Elevate Your Stay, Premium Studio | Chicago

apartment - Chicago
This Magnificent Mile apartment rental is steps from Oak Street Beach and a short walk from Michigan Avenue and Millennium Park.
The unit offers a queen-size bed, sleeper sofa, full kitchen with dishwasher and in-unit washer/dryer, private balcony, and accommodates two guests, plus pets for a fee; on-site parking is available for an additional $51 per night.
Mccormick Apt 3br Corner Oasis Near Soldier Field - Chicago
9.7 87 reviews
Chicago
7 3
$445/nighttotal: $1335 (3 )

Mccormick Apt 3br Corner Oasis Near Soldier Field

apartment - Chicago
This 3-bedroom apartment is located in the South Loop district of Chicago, just steps away from McCormick Place and a short walk from the nearest subway station. The apartment comfortably sleeps 8 guests with 3 queen-size beds and a sofa bed, features modern amenities such as 4K smart TVs with Netflix and Roku in all rooms, a fully equipped kitchen, a washer and dryer in the unit, and access to a gym and 24/7 security.

Find the Best Family-Friendly Lodgings in Chicago

Stay near Millennium Park or the Shedd Aquarium for easy access to world-class museums. These apartments offer extra bedrooms and full kitchens, making logistics simple near the Lakefront Trail and Navy Pier.

King Bed 6br Chicago With Pool Table Sleeps 16 Near Humboldt Park - Chicago
8.7 3 reviews
Chicago
10 6
$1159/nighttotal: $6954 (6 )

King Bed 6br Chicago With Pool Table Sleeps 16 Near Humboldt Park

apartment - Chicago
This apartment is located near Humboldt Park in Chicago, offering easy access to the park's attractions.
This 3000 square foot residence accommodates up to 31 guests with 1 bedroom and 3 bathrooms, featuring a full kitchen, complimentary Wi-Fi, and on-site billiards.
Lux Lincoln Park 2bd/2.5ba (+Parking) - Chicago
9.9 98 reviews
Chicago
6 2
$593/nighttotal: $2965 (5 )

Lux Lincoln Park 2bd/2.5ba (+Parking)

apartment - Chicago
This luxurious, newly renovated two-level apartment is located in Chicago's Lincoln Park neighborhood, between North and Armitage Avenues, a short distance from the Red and Brown Line stations and Lake Michigan.
The 2-bedroom, 2-bathroom unit sleeps six, features a chef's kitchen with stainless steel appliances, a king-size bed with a 14-inch Novaform mattress, two queen beds with 10-inch Novaform mattresses, fast WiFi (800+ Mbps), smart TVs, a children's playroom, and on-street parking with provided permits.
Spacious Theater And Game Room Retreat - Charming Luxury Escape - Chicago
Chicago
4 4
$1741/nightfor 1 night

Spacious Theater And Game Room Retreat - Charming Luxury Escape

house - Chicago
This house is located in Chicago's Belmont-Cragin neighborhood, 1.8 miles from Riis Park and 9.5 miles from Chicago O'Hare International Airport.
This family-friendly dwelling accommodates up to 11 guests with 4 bedrooms and 2 bathrooms, featuring a private home theater, arcade game room, home gym, outdoor lounge with a grill and firepit, and a dedicated workspace, with a Pack 'n Play and high chair available upon request.
Gold Coast Pristine 5br|3.5ba| Patio| Parking - Chicago
10 16 reviews
Chicago
10 5
$1662/nighttotal: $4986 (3 )

Gold Coast Pristine 5br|3.5ba| Patio| Parking

apartment - Chicago
This multi-level Gold Coast residence is situated in a prestigious Chicago neighborhood known for its historic mansions, high-end boutiques, and acclaimed restaurants, just a short distance from the Lake Michigan shoreline and notable architectural sites.
This family-friendly apartment accommodates up to 12 guests with 5 bedrooms and 3 bathrooms, featuring a fully stocked kitchen, free garage parking, a professionally landscaped yard with a deck for outdoor entertaining, and access to an indoor fitness center and rooftop area.

Frequently Asked Questions about short term rentals in Chicago

  • Which top landmarks you shouldn't miss in Chicago, IL?

    You definitely want to check out the iconic Willis Tower, formerly known as Sears Tower, for panoramic city views. The Art Institute of Chicago is a must-see for art lovers, and Millennium Park is home to the famous Cloud Gate sculpture, affectionately known as 'The Bean.'
  • What are the best short term rentals in Chicago?

  • What's the best district to book a short term rental in Chicago?

    For short-term rentals in Chicago, the best district would be the Loop. It's the downtown area and offers proximity to major business centers, theaters, and cultural institutions.
  • What kind of weather can travelers expect in Chicago, IL?

    Chicago has four distinct seasons. Summers are hot and humid, with temperatures often reaching the 80s. Winters are cold and snowy, with temperatures often below freezing. Spring and fall are mild and pleasant, with temperatures in the 50s and 60s.
  • What are the best short term rentals with a pool in Chicago?

  • What are the most affordable attractions to visit in Chicago?

    The most affordable attractions to visit in Chicago include exploring Millennium Park, visiting the Art Institute of Chicago on free admission days, and enjoying the scenic views from Navy Pier.
  • What are the most popular festivals and events in Chicago, IL?

    Chicago is known for its vibrant festival scene. The Chicago Blues Festival is a major event, and the Taste of Chicago is a great way to sample the city's diverse culinary offerings. The Lollapalooza music festival is a huge draw for music fans.
  • What are the best short term rentals with a jacuzzi in Chicago?

  • How accessible are attractions and amenities for families with strollers or wheelchairs in Chicago?

    Most attractions and amenities in Chicago are accessible for families with strollers or wheelchairs.
  • Are there any famous stadiums or sports arenas in Chicago, IL?

    Chicago is a major sports city. Wrigley Field is home to the Chicago Cubs baseball team, and Guaranteed Rate Field is home to the Chicago White Sox. The United Center is home to the Chicago Bulls basketball team and the Chicago Blackhawks hockey team.
  • What are the best short term rentals for families and kids in Chicago?

    The best short term rentals for families and kids in Chicago are 2bd/2ba Mag Mile Masterpiece (+Rooftop), Kasa South Loop Chicago and Sonder South Wabash.

  • Are popular attractions more affordable in off-peak season in Chicago?

    Popular attractions in Chicago may be more affordable in the off-peak season, which is typically during the winter months.
  • What notable natural landmarks are near Chicago, IL?

    The Indiana Dunes National Park is a short drive from Chicago and offers beautiful beaches, hiking trails, and scenic views of Lake Michigan. The Morton Arboretum is a great place to explore different types of trees and plants.
  • What are the top nightlife spots and party destinations in Chicago?

    For the best party travel experience in Chicago, head to River North for its upscale nightclubs and trendy bars. Wicker Park and Logan Square are also fantastic for a more laid-back, hipster vibe with plenty of dive bars and live music venues.
  • What part of Chicago, IL is ideal for finding lodging?

    The River North neighborhood is a popular choice for its trendy restaurants, bars, and art galleries. The Magnificent Mile is another great option, with its upscale shopping and dining. If you're looking for a more budget-friendly option, consider staying in the Wicker Park or Bucktown neighborhoods.
  • What are the most popular festivals and events in Chicago for party lovers?

    For party lovers, Lollapalooza is a must-attend music festival held every summer in Grant Park. Chicago Pride Parade and Northalsted Market Days in Boystown are also huge events that draw lively crowds and offer a fantastic party atmosphere.
  • Are there any outdoor sports activities that one can participate in while visiting Chicago?

    While visiting Chicago, you can enjoy outdoor sports activities like kayaking on the Chicago River, biking along Lake Michigan, or playing beach volleyball at North Avenue Beach.

Popular destinations

Best Chicago Short term rentals with a jacuzzi

Among the 13281 accommodations in Chicago, here are the 4 best rentals with a jacuzzi

Dual Penthouse Retreat: Perfect For Groups - Chicago
Chicago
10 6
$2137/nighttotal: $6411 (3 )

Dual Penthouse Retreat: Perfect For Groups

apartment - Chicago
This six-bedroom, five-bathroom West Loop condo is located near Union Park and Fulton Market, offering direct access to Jewel Osco via a private footbridge and within a five-minute drive of Randolph Street Market and Fulton Market.
This expansive residence accommodates up to 14 guests with multiple king and queen beds, rollaway options, a chef's kitchen, two private balconies, and access to building amenities including an HD movie theater, outdoor pool, terrace lounge with fire pit, and exercise facility with steam room.
6 Luxe Apts, Perfect Group Solution, Sleeps 30 - Chicago
Chicago
10 13
$4941/nighttotal: $14823 (3 )

6 Luxe Apts, Perfect Group Solution, Sleeps 30

apartment - Chicago
This expansive 13-bedroom, 12-bathroom residence is located in Chicago's West Loop, a 7-minute walk to Union Park and a 10-minute walk to Michelin-star restaurants, placing it within walking distance of Soho House and Google HQ.
This large rental offers accommodation for up to 32 guests and features 30,000 sq. ft. of amenities including a swimming pool, spa, firepits, yoga deck, golf simulator, and a fitness center, with co-working spaces and private offices also available.
High-end 3br Retreat + Steps To Millennium Park - Chicago
Chicago
4 3
$1747/nighttotal: $6988 (4 )

High-end 3br Retreat + Steps To Millennium Park

apartment - Chicago
This 3-bedroom, 2-bathroom condo in Chicago's Loop district offers top-floor train and city views, placing you within a 15-minute walk of Millennium Park, an 8-minute walk to the Chicago Theatre, and a 20-minute walk to Navy Pier.
This family-friendly residence accommodates up to 6 guests with a fully-equipped chef's kitchen, air conditioning, internet, a swimming pool, jacuzzi, terrace, fitness center, and parking, complemented by building amenities like a sky lounge and a two-story social room.
Streeterville Studio W Gym Pool Nr Navy Pier Chi-450 - Chicago
10 1 review
Chicago
2 1
$166/nighttotal: $9960 (60 )

Streeterville Studio W Gym Pool Nr Navy Pier Chi-450

studio - Chicago
This Streeterville apartment is located 0.2 miles from Ohio Street Beach, 0.8 miles from 360 Chicago, and a 13-minute walk from Water Tower Chicago, with proximity to Navy Pier and the Chicago Museum of Contemporary Art.
This 590 square foot studio apartment accommodates up to 3 guests with a full kitchen, air conditioning, and complimentary WiFi, and features access to a fitness center.

Neighborhoods and points of interest in Chicago

Our Favorite Luxury Short-Term Rentals in Chicago

Live in the heart of the Gold Coast or Streeterville in rentals featuring floor-to-ceiling windows and high-end finishes. These units place you steps from the Magnificent Mile and Michelin-starred dining in the West Loop.

The Neighborhood Hotel-little Italy - Chicago
9.6 288 reviews
Chicago
2 1
$351/nighttotal: $2457 (7 )

The Neighborhood Hotel-little Italy

aparthotel - Chicago
This 3.5-star Chicago Near West Side apartment hotel is located less than a mile from Rush University Medical Center and within three miles of the United Center and Millennium Park, offering easy access to public transportation.
Each apartment features a kitchenette with a refrigerator, stovetop, microwave, and dishwasher, plus a smart TV with satellite channels, a sitting area, and coffee/tea maker; on-site laundry facilities are also available.
Kasa Magnificent Mile Chicago - Chicago
9.2 1517 reviews
Chicago
10 4
$1308/nighttotal: $3924 (3 )

Kasa Magnificent Mile Chicago

aparthotel - Chicago
Kasa Magnificent Mile Chicago is located on the Magnificent Mile, a bustling shopping and dining district, just a short walk from the Shops at Northbridge, CIBC Theatre, and Millennium Station. This aparthotel boasts excellent user ratings for its location, cleanliness, and overall experience.
The apartment features modern amenities like a flat-screen TV, air conditioning, and a private bathroom. Guests can enjoy a terrace or balcony, a garden, a fitness center, and a restaurant.
Kasa Lake Shore Chicago - Chicago
9.4 3 reviews
Chicago
2 1
$337/nighttotal: $2359 (7 )

Kasa Lake Shore Chicago

aparthotel - Chicago
This aparthotel is located in Downtown Chicago, offering proximity to Ohio Street Beach, Michigan Avenue, and Lake Michigan, all within a 0.19-mile walk, with Grant Park and Navy Pier also a short distance away.
This lodging provides fully equipped kitchens, in-unit washers/dryers, and a rooftop terrace, with convenient access to public transportation and on-site self-parking.
Kasa South Loop Chicago - Chicago
9.4 3240 reviews
Chicago
3 1
$273/nighttotal: $1092 (4 )

Kasa South Loop Chicago

aparthotel - Chicago
Kasa South Loop Chicago is located in the South Loop neighborhood, just a short walk from DePaul University and a quick drive from attractions like Willis Tower and the Art Institute of Chicago. The aparthotel has excellent ratings for location, cleanliness, and overall user experience.
The apartments are spacious and well-equipped with kitchens, seating areas, and private bathrooms. Guests can enjoy amenities like a swimming pool, fitness center, and a sun terrace, along with free Wi-Fi and a business center.

Guest-Favorite Dog-Friendly Lodgings in Chicago

Book a stay near the off-leash areas of Grant Park or the shaded paths of Lincoln Park. These rentals provide immediate access to the Lake Michigan shoreline and pet-friendly cafes in neighborhoods like Wicker Park.

Spacious 3br: Easy Street Parking & Walk To Train - Chicago
9.9 218 reviews
Chicago
5 3
$807/nighttotal: $2421 (3 )

Spacious 3br: Easy Street Parking & Walk To Train

apartment - Chicago
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