Chicago, IL Short term rentals

13281 available short term rental offers

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Chicago, IL short term rentals
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Best Short term and Weekly rentals in Chicago, IL

Top-Rated Short-Term Rentals in the Old Town of Chicago, IL

Stay footsteps from popular independent bistros and excellent transit connections at central short-term rentals in Chicago, IL.

2 Pet-friendly Units! Near Chicago Riverwalk - Chicago, IL
9.5 16 reviews

2 Pet-friendly Units! Near Chicago Riverwalk

B&B, Chicago
This Chicago guesthouse is conveniently located in the downtown area, near the Chicago River, within easy walking distance of numerous bars and restaurants and a few kilometres from Soldier Field, Wrigley Field, and the United Centre.
Offering two bedrooms and two bathrooms, this pet-friendly lodging sleeps up to eight guests and boasts modern amenities including free Wi-Fi, flat-screen TVs, and an on-site restaurant, Hoyt's American Tavern.
*Steps To Mag Mile, 2 Bd , Fast Wi-fi, W&d - Chicago, IL
9.9 226 reviews

*Steps To Mag Mile, 2 Bd , Fast Wi-fi, W&d

apartment, Chicago
This Gold Coast flat is situated on Michigan Avenue, a short walk from Oak Street Beach and close to Chicago's 'L' train and express bus services.
The two-bedroom apartment, sleeping four, includes a kitchen with dishwasher, in-unit laundry, Wi-Fi, and a smart TV; hourly rate garage parking is available nearby.
Downtown Chicago Stay With Free In & Out Parking 1 - Chicago, IL
9.0 40 reviews

Downtown Chicago Stay With Free In & Out Parking 1

apartment, Chicago
This four-bedroom, two-bathroom flat is centrally located in downtown Chicago, just 500 metres from the Chicago Riverwalk and 500 metres from Millennium Park, with Willis Tower 1.9 kilometres away and Museum Campus 2.1 kilometres away.
This expansive 129 square metre modern apartment accommodates up to ten guests and includes a fully equipped kitchen, air conditioning, Wi-Fi, on-site parking, and access to a fitness centre.
River North | Rooftop With In & Out Parking | 1 - Chicago, IL
9.7 114 reviews

River North | Rooftop With In & Out Parking | 1

apartment, Chicago
This two-bedroom Chicago apartment is centrally located in downtown Chicago, offering easy access to various attractions.
The 93-square-metre (1000 sq ft) flat sleeps six, boasting two queen beds, a sofa bed, and an inflatable mattress, plus a fully equipped kitchen, free parking, and access to a fitness centre and rooftop terrace with BBQ facilities.

Check Out Family-Friendly Holiday Lets in Chicago, IL

Getting the accommodation right makes all the difference for a family trip to Chicago, IL. City attractions within easy reach at these options.

Prime Wrigley Spot Workspace - Chicago, IL
9.7 32 reviews

Prime Wrigley Spot Workspace

apartment, Chicago
This three-bedroom flat is located in Chicago's Wrigleyville district, a mere 500 meters from Wrigley Field and adjacent to The Metro concert venue, offering straightforward access to the city's transport network.
This property accommodates up to seven guests, providing a fully equipped kitchen, two bathrooms, air conditioning, and WiFi, with parking available and a dedicated workspace for those needing to work remotely.
Private Roof Deck And Dual Kitchens - Stunning Oasis - Chicago, IL
No reviews

Private Roof Deck And Dual Kitchens - Stunning Oasis

apartment, Chicago
This River North flat offers exclusive private floor access in Chicago, situated a mere 500 meters from Michigan Avenue and the Magnificent Mile, with the iconic Navy Pier and Millennium Park's Cloud Gate (The Bean) also within easy walking distance.
This spacious accommodation, ideal for up to 16 guests, boasts 4 bedrooms and 3 bathrooms spread across two suites, featuring 10 Queen beds, two full kitchens, air conditioning, Wi-Fi, two private garage parking spaces, and a private rooftop deck, all recently refurbished with modern amenities.
Private Lincoln Square Garden Apt - Chicago, IL
9.8 498 reviews

Private Lincoln Square Garden Apt

B&B, Chicago
This charming garden apartment is situated in a lively neighbourhood close to Lincoln Square, just a short walk from the train station and the Old Town School of Folk Music. It has received excellent ratings for cleanliness, location and user experience.
The apartment has one bedroom and one bathroom, comfortably accommodating up to four guests. It offers a kitchenette with a microwave, coffee maker, toaster and mini-fridge, as well as a shared front yard with a bench and picnic table. The apartment also benefits from a portable air conditioner, shared laundry facilities, and a tree swing and treehouse for children.
Cozy Home Near Ohare Fast Internet - Chicago, IL
9.2 137 reviews

Cozy Home Near Ohare Fast Internet

apartment, Des Plaines
This Des Plaines property is conveniently located just a short distance from O'Hare Airport, Allstate Arena, and Rivers Casino, making it an ideal choice for travellers seeking easy access to these attractions. The surrounding neighbourhood is safe and peaceful, offering a relaxing atmosphere. The property has consistently received excellent ratings from guests for its cleanliness, location, and overall experience.
The house features three bedrooms and two bathrooms, comfortably accommodating up to six guests. The property offers a range of amenities, including a fully equipped kitchen, a spacious backyard with a gas grill, and free parking, ensuring a comfortable and enjoyable stay.

Frequently asked questions about short term rentals in Chicago, IL

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

    You definitely want to see the iconic Willis Tower, formerly known as the Sears Tower, and the impressive Art Institute of Chicago. And don't forget to take a stroll along Navy Pier, especially at night when the lights come on.
  • What are the best short term rentals in Chicago, IL?

  • What kind of weather can travelers expect in Chicago, IL?

    Chicago has four distinct seasons. Summers are hot and humid, with temperatures averaging around 25°C. Winters are cold and snowy, with temperatures often dropping below freezing. Spring and autumn are mild and pleasant, with temperatures ranging from 10°C to 20°C.
  • What are the best short term rentals with a pool in Chicago, IL?

  • What are the most popular festivals and events in Chicago, IL?

    Chicago is known for its vibrant festivals and events. Some popular ones include the Chicago Blues Festival, the Lollapalooza music festival, and the Taste of Chicago food festival. There's also the Chicago Air and Water Show, which takes place every August.
  • What are the best short term rentals with a jacuzzi in Chicago, IL?

  • Are there any famous stadiums or sports arenas in Chicago, IL?

    Chicago is a big sports city! You've got Wrigley Field, home to the Chicago Cubs baseball team, and Guaranteed Rate Field, home to the Chicago White Sox. And for basketball fans, there's the United Center, home to both the Chicago Bulls and the Chicago Blackhawks.
  • What are the best short term rentals for families and kids in Chicago, IL?

  • What notable natural landmarks are near Chicago, IL?

    Just a short drive from Chicago, you can find Indiana Dunes National Park, which features sandy beaches, towering dunes, and a variety of wildlife. You can also visit the Morton Arboretum, a beautiful botanical garden with over 1,700 species of trees and plants.
  • What part of Chicago, IL is ideal for finding lodging?

    The River North neighbourhood is popular with travellers, offering a mix of hotels, restaurants, and art galleries. If you're looking for something more budget-friendly, the Lincoln Park area has a good selection of hotels and hostels.

Popular destinations

Browse Holiday Lets with a Jacuzzi in Chicago, IL

These short-term lets in Chicago, IL come with a hot tub or jacuzzi, ideal for a relaxing hot tub soak at the end of a long day exploring.

Top Floor Views + Central Comfort - Chicago, IL
No reviews

Top Floor Views + Central Comfort

apartment, Chicago
This top-floor flat in Chicago offers exceptional city views and is situated just 400 metres from Union Station and 800 metres from the Willis Tower.
This modern apartment accommodates up to six guests with two bedrooms and two bathrooms, featuring a designer kitchen with premium appliances, a 75-inch television, and access to building amenities including a fitness centre, game room, and an outdoor sky terrace with grills and firepits.
Irving Park/avondale Updated Vintage Top Unit - Chicago, IL
9.9 105 reviews

Irving Park/avondale Updated Vintage Top Unit

apartment, Chicago
This Chicago apartment is conveniently located in a residential area, approximately 1.6km from Wrigley Field, 0.6km from the I-90/94 highway, and a short distance from the Blue Line.
The two-bedroom flat sleeps six guests, boasting a queen-size sofa bed, a private balcony, access to a shared backyard with a basketball court, and upcoming outdoor amenities including a pizza oven and space heater; free street parking is also available.
Sky-high 2br W/ Gym & City Views - Chicago, IL
No reviews

Sky-high 2br W/ Gym & City Views

apartment, Chicago
This two-bedroom flat is located in Chicago's Fulton Market district, a 10-minute walk from Union Park and Google HQ.
This apartment offers access to 2800 square meters of building amenities including a swimming pool, spa, yoga deck, and fitness centre, and sleeps up to five guests with its two Queen bedrooms and private balcony.
2br Near Riverwalk + Downtown Access - Chicago, IL
10 3 reviews

2br Near Riverwalk + Downtown Access

apartment, Chicago
This Magnificent Mile apartment in downtown Chicago offers a luxurious stay close to Washington Square Park, Jane Byrne Plaza, and the Museum of Contemporary Art.
The 117 m² dwelling boasts two bedrooms, two bathrooms, sleeps up to seven guests, and includes a fully equipped kitchen with high-end appliances, a balcony with city views, and access to a building with a heated pool, hot tub, and fitness centre.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL luxury short term rentals

Kasa Magnificent Mile Chicago - Chicago, IL
9.2 1582 reviews

Kasa Magnificent Mile Chicago

aparthotel, Chicago
Kasa Magnificent Mile Chicago is situated on the Magnificent Mile, a short walk from the Shops at Northbridge and just over a mile from North Avenue Beach, making it ideal for exploring Chicago's attractions and enjoying the lakefront. This aparthotel consistently receives excellent ratings for its location, cleanliness, and overall experience.
The accommodation offers spacious rooms with desks, comfortable furnishings, and private bathrooms. Amenities include a kitchen with a fridge, freezer, microwave oven, and dishwasher, as well as air conditioning, a terrace or balcony, a garden, a concierge, a restaurant, a fitness centre, and parking.
Kasa Lake Shore Chicago - Chicago, IL
8.2 30 reviews

Kasa Lake Shore Chicago

aparthotel, Chicago
This 4-star aparthotel in Downtown Chicago offers a prime location, situated a short walk from Ohio Street Beach, Michigan Avenue, and Lake Michigan, with Grant Park and Navy Pier within 1.5 kilometres.
Each apartment provides a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside an in-room washer/dryer, and the property features a rooftop terrace with city views.
Kasa South Loop Chicago - Chicago, IL
9.4 3184 reviews

Kasa South Loop Chicago

aparthotel, Chicago
Kasa South Loop Chicago is situated in the South Loop, a short walk from DePaul University and within a mile of the CIBC Theatre, offering easy access to the city's vibrant attractions. This aparthotel has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The accommodation features modern, comfortable apartments with fully equipped kitchens, including a dishwasher, and a separate living area with a flat-screen TV. Guests can enjoy a range of amenities, such as a swimming pool, a fitness centre, a garden, and a terrace, as well as a business centre and a restaurant.
The Neighborhood Hotel-little Italy - Chicago, IL
9.6 327 reviews

The Neighborhood Hotel-little Italy

aparthotel, Chicago
This Near West Side serviced apartment is situated less than 1.6km from Rush University Medical Centre and within 4.8km of both the United Centre and Millennium Park.
The self-catering apartments feature kitchenettes with fridges, microwaves, and dishwashers, smart TVs with satellite channels, and free Wi-Fi in public areas; guests also benefit from proximity to public transport links, including Polk and Racine train stations.

Best Short-Term Rentals with Parking in Chicago, IL

Parking is sorted from the start. Every short-term let in Chicago, IL includes free on-site spaces.

Modern + Cozy Garden Apt W/garage Parking, 20m Dt - Chicago, IL
9.7 35 reviews

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

apartment, Chicago
Bright 2+ Bed 2 Bath Home Away From Home - Chicago, IL
10 1 review

Bright 2+ Bed 2 Bath Home Away From Home

apartment, Chicago
Lovely 1 Bedroom W/ Office Space And Free Parking. - Chicago, IL
9.9 187 reviews

Lovely 1 Bedroom W/ Office Space And Free Parking.

apartment, Chicago
O'hare/downtown|2br 3-beds|blue Line|easy Parking - Chicago, IL
9.8 41 reviews

O'hare/downtown|2br 3-beds|blue Line|easy Parking

apartment, Chicago

Our Favourite Pet-Friendly Short-Term Rentals in Chicago, IL

Explore with your best friend by your side; book a pet-friendly short-term rental in Chicago, IL that feels like a home away from home for you both.

1br W/ In-unit Laundry + Steps To Transit - Chicago, IL
9.3 32 reviews

1br W/ In-unit Laundry + Steps To Transit

apartment, Chicago
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