Chicago, Illinois, stands out as one of the Midwest's most vibrant cities and ranks among America's great urban destinations. Its celebrated architecture, more than forty museums, and close to 7,000 restaurants—serving icons like Chicago deep-dish pizza and the classic Chicago hot dog—make it a thrilling place to visit. Once you've settled on the right short-term rental in Chicago, the trip becomes even better.
Planning a getaway isn't complete without deciding where you'll sleep. Hotels tend to be pricey and hostels are in short supply, so short-term rentals in Chicago are a smart alternative.
Below, options are grouped by group size, style, atmosphere, and budget to make your search easier. Ready to find the ideal Chi-Town rental?
Let's dive in.
Next up: choosing your base.
At a Glance: Five Standout Chicago Rentals
Best Overall Value: Studio with Private Outdoor Hot Tub
- Price: $$
- Sleeps 2
- Private hot tub and yard
- Quiet setting
Best for Budget Travelers: A Budget Traveler's Dream Room
- Price: $
- Sleeps 2
- Walkable to public transit
- Billiards room
Most Luxurious: Zen Loft in Downtown
- Price: $$$$
- Sleeps 10
- Seven TVs
- Gourmet kitchen
Best for Solo Travelers: Spacious Apartment in Safe Neighborhood
- Price: $
- Sleeps 2
- Lively neighborhood
- Free parking
Ideal for Digital Nomads: Private Room in Sunny Artist Loft
- Price: $
- Sleeps 2
- Impressive outdoor garden
- Full kitchen
What Chicago Rentals Offer
Chicago has a huge number of short-term rentals in a wide range of styles. You'll find trendy modern lofts downtown as well as listings that feel more like suburban houses, so there's an option for nearly every budget and preference in the Windy City.
Central Chicago rentals usually cost more, but that's the trade-off for proximity to top attractions. Choosing a place a bit farther out can free up cash for food and exploring.
With hundreds or even thousands of choices, you should be able to find a cool place for your trip quickly. Here's a closer look at what to expect when planning your Chicago stay:
Apartments are the most common type of accommodation in Chicago, which makes sense for a major metropolis. From small, older studios to modern lofts large enough for big groups, prices vary widely.
Newer, bigger apartments in the city center cost more than shabbier options in other neighborhoods. If you're budget-conscious, the best places to stay in Chicago might not be where you'd expect.
If you don't mind being a little away from the action, you can spend your Chicago trip in an actual house. While the best rentals inside the city are apartments, several nearby suburbs often have houses available.
Private rooms are extremely common among Chicago rentals and you'll see many while browsing. A private room is essentially a room in a shared apartment or home. Some are more like mini studios, while others are just a room.
The 15 Top Chicago Rentals
Whether you're visiting Chicago for a short stay or hoping to stay long-term, there's an iconic rental waiting. To simplify your search, here are the best Chicago rentals for all types of travel.
Studio with Private Outdoor Hot Tub | Best Overall Value
- Price: $$
- Sleeps 2
- Private hot tub and yard
- Quiet setting
This entire-unit rental is a rare find in Chicago and offers far more than its listing price suggests. Settle into a striking modern design with a truly iconic amenity: a fully functional outdoor hot tub. Yes, this spacious apartment really does have a yard, a rarity in this dense city. It also provides easy access to Chicago's best activities.
A full kitchen lets you save on dining out if you choose, and high-speed internet plus common areas filled with natural light make this an excellent base for digital nomads. The bed is comfortable, and the quality is high enough that it's designated as an "Airbnb Plus" listing.
It's also in a beautiful, safe neighborhood close enough to tourist spots but far enough for a genuine local experience. You can walk easily to Wicker Park or jog in the larger Humboldt Park. All of this makes the studio the best overall value among Chicago rentals.
A Budget Traveler's Dream Room | Best Budget Option
- Price: $
- Sleeps 2
- Walkable to public transit
- Billiards room
This private-bedroom rental in Chicago is a wonderful budget choice for travelers who want to save money for deep-dish pizza—the real highlight of any Chicago itinerary.
Guests stay in a historic Victorian-era home just a 3-minute walk from public transit. The room has a king-size bed and a sofa bed for groups larger than two. Guests may also use the full-size kitchen and both the indoor and outdoor living areas.
There's even a billiards room for a game of pool. With ample space, fast Wi-Fi, and an unbeatable price, it's one of the best Chicago rentals for a backpacker's budget.
Zen Loft in Downtown | Most Luxurious
- Price: $$$$
- Sleeps 10
- Seven TVs
- Gourmet kitchen
This four-bedroom, two-bathroom loft in Old Town Chicago is drool-worthy: 3,500 square feet of zen-like heaven. The artwork and furnishings—a mix of industrial and magazine-worthy pieces—make this Chicago rental a haven for Instagram-ready shots.
There are four queen beds and one full bed, plus air mattresses and baby cribs available. A total of seven TVs, including two 75-inch sets, are spread throughout this enormous apartment. The price is certainly not cheap, but it becomes relatively affordable for a large group.
Spacious Apartment in Safe Neighborhood | Perfect for Solo Travelers
- Price: $
- Sleeps 2
- Lively neighborhood
- Free parking
This one-bedroom, one-bathroom short-term rental in Chicago is ideal for solo travelers. It's a small studio with hardwood floors—sweet and simple. A kitchenette includes all the basics, including coffee for java fans.
If you're looking for a budget stay as a solo traveler with no frills, this is the Chicago rental for you. Located in Pilsen Westside, the area is full of arts, culture, and delicious food, not far from Downtown. A 15-minute ride on public transportation gets you to Chicago's top sights.
Private Room in Sunny Artist Loft | Perfect for Digital Nomads
- Price: $
- Sleeps 2
- Impressive outdoor garden
- Full kitchen
This sunny artist's loft is a dream for digital nomads. It looks like something from a mood board, with dozens of stunning plants inside the apartment and on the lovely outdoor deck. The property features a comfy king-sized bed with shared spaces, making it a social spot perfect for connecting with other unique travelers.
The location is nearly unmatched, with plenty of delicious restaurants nearby, and both the Chicago River and lakefront within walking distance. You'll also have convenient public transport access to reach virtually anywhere you want to visit in Chicago. Don't miss a chill evening on the deck—a blissful space that couldn't be more floral in summer.
The studio has a particularly artistic bent, so expect unique vibes and an absolutely perfect space for creation of any kind. You won't find lighting like this in any other Chicago rental. With a comfy queen-sized bed and a room filled with sunlight, you're staying in digital nomad heaven.
More Great Chicago Rentals
Here are a few more favorites in Chicago.
Artsy Apartment with Funky Vibes | Best for Couples
- Price: $$
- Sleeps 2
- Unique artwork and atmosphere
- Private free parking
This one-bedroom, one-bathroom Chicago apartment is perfect for a couple's getaway. It's in the Wicker Park/Bucktown community, one block from the subway and close to great eateries and shops. It features a comfortable queen-sized bed, plus a refrigerator and microwave to store and reheat amazing Chicago leftovers.
This beautiful home makes for a memorable stay for couples visiting the Windy City—private, clean, comfortable, and reasonably priced for what you get. With free private parking included, it's the best Chicago rental for lovebirds.
Aloha Dreamy Paradise | Best for a Group of Friends
- Price: $$$
- Sleeps 10
- Giant neon palm tree sign
- Skylights and high ceilings
This four-bedroom, two-bathroom Chicago rental has five beds total. It's in the heart of Wicker Park, where there's endless things to do and see. The decor is super fun, with an enormous neon palm tree sign and a giant pink shark on the walls. The entire apartment seems to come from a Hollister magazine, with bright furnishings and quirky knick-knacks from seashells to tiki statues.
The kitchen is stocked with everything you need, going beyond the basics with a blender and a waffle maker.
Artsy Apt with Great Value | Top Value in Lincoln Park
- Price: $$
- Sleeps 2
- HDTV and high-speed Wi-Fi
- Quality air conditioning
This one-bedroom, one-bathroom studio apartment in Lincoln Park is packed with value. Fantastic food and vibrant nightlife are just outside the doorstep. The Orange Cafe is on the same block for a fabulous brunch, or Trader Joe's is up the block if you want goodies to cook in the fully equipped kitchen. It's a very comfortable space with a cozy bed filled with artsy touches from pillows to paintings.
An extra air mattress can be provided if an additional guest joins.
Sunny Room in Central Apt | Best Homestay
- Price: $
- Sleeps 2
- Free parking space provided
- Memory foam mattress
Located in the heart of downtown with easy self-check-in and free luggage drop-off, this is an incredible Chicago homestay. The hosts allow early check-in as early as 11:00 am and provide a free parking spot.
The location is truly incredible: a five-minute walk to the University of Illinois Chicago and a five-minute walk to public transportation. It's also a quick metro ride to Downtown.
Since it's not in the heart of Downtown, it's quiet enough that you won't hear any nighttime shenanigans outside. Enjoy a peaceful night's sleep in this beautifully designed Chicago rental that will quickly feel like home.
Modern Room in the Heart of Loop | Best for Nightlife
- Price: $
- Sleeps 2
- Full apartment access
- Free coffee and tea
Chicago is home to hundreds of incredible bars and pubs, quite a few of which are now city landmarks. If you head Downtown, you'll be surrounded by incredible nightlife, from the Tiki bar Three Dots and a Dash to the London House Rooftop Bar to the glitzy Z Bar. It's hard to pick just one bar, so go ahead and visit a few.
This one-bedroom with one private bathroom room rental in a Chicago apartment is the perfect place to stay close to all the nightlife. The room itself is spacious with high ceilings. Guests are also allowed to use the apartment to the fullest, enjoying the kitchen, dining room, living room, and laundry facilities. This is just a two-bedroom, two-bathroom apartment, so you only share it with the hosts themselves.
Stunning Downtown Artist Loft | Amazing Luxury Option
- Price: $$$
- Sleeps 2
- Brick and timber styled loft
- Washer and dryer
This one-bedroom, one-bathroom apartment in the West Loop of Downtown Chicago is a dream. It has a rustic vibe with exposed brick walls and moody lighting, yet modern furnishings and tasteful touches. It's a 900-square-foot traditional brick and timber loft with all the amenities you could need. The washer and dryer make your stay even easier, and the minibar and Keurig machine are great additions.
This big, open, stylish loft is the answer to all your Chicago travel problems.
Stylish Apt. w/ Thoughtful Touches | Best for Families
- Price: $$
- Sleeps 8
- Modern space with custom comforts
- High chair and crib
This three-bedroom, one-bathroom Chicago apartment comes with four beds total. If you and your big family are heading to Chicago, this is the rental for you. There's a free parking space in the garage, a fully equipped kitchen, and even a high chair for the kids. High-speed Wi-Fi at 250-350 MB/sec means the kids won't complain about the internet struggling to load My Little Pony on YouTube.
Situated in the South Loop, you'll be less than 3km from Grant Park, the Art Institute of Chicago, and the Field Museum of Natural History. This is one of the best Chicago rentals in terms of furnishings and facilities, filled with thoughtful touches that will make you and your family feel at home.
Spacious Apt By Millennium Park | Best in Downtown Chicago
- Price: $$$
- Sleeps 2
- Ideal location facing Michigan Ave
- Gym and pool access
Spacious and minimalist, this one-bedroom, one-bathroom Chicago apartment is right by Millennium Park, facing Michigan Ave. It's less than a 10-minute walk to incredible Chicago tourist hot spots, from the Art Institute to Grant Park. If you're traveling without a car and don't want to deal with metro cards and long walks, this is the Chicago rental for you.
Moreover, this Chicago apartment is well-equipped to make your stay extra comfortable, from complimentary breakfast items to plenty of clean towels to a TV with Netflix already hooked up. In the building, you can use the indoor pool and the 24-hour gym. There's also a doorman on-site 24 hours a day for added safety.
Calm Studio in Downtown Core | Another Great Downtown Apartment
- Price: $$
- Sleeps 2
- 2 minutes to Millennium Park
- Great views from the apartment
This one-bedroom, one-bathroom studio apartment is perfectly located right in the heart of Downtown. Seriously, it couldn't be more Downtown than this—a truly unbeatable location. Sightseeing is all within a two-minute walk, and Pizzano's around the corner serves famous Chicago deep-dish pizza. This Chicago apartment is just what you're looking for. It includes all the basics, from fuzzy towels to a fully equipped kitchen.
You'll be sitting pretty in this Chicago rental.
Picturesque Master Suite w/ Hot Tub | Runner-Up Homestay
- Price: $
- Sleeps 2
- Hot tub
- Private bathroom with bathtub
This private room rental is a wonderful Chicago homestay. This short-term rental is a large master suite with plenty of space to move around and breathe. Located just outside the center of Chicago, it's a ten-minute metro ride to downtown or other popular tourist spots from Millennium Park to the Willis Tower.
The private bathroom is divine, complete with a bathtub and a shower, so you can enjoy a warm bubble bath after a long day exploring Chicago. This host also allows last-minute reservations, cancellation within 24 hours for a free refund, and no security deposit. So if you're a little unsure about your travel specifics, this Chicago rental is the one for you. What's better than a rental with a hot tub? (Well, a rental with two hot tubs and a helipad—but I can't find one.)
Don't Forget Your Chicago Travel Insurance
I know paying for insurance is no fun. But neither is paying medical bills.
Trust me, you don't want to know what that experience is like in the USA. Just get insured.
Final Thoughts on Chicago Rentals
Chicago is quite a fun city to visit. With plenty of skyscrapers, fantastic museums, and some of the best food in the USA, there is very nearly too much to do in Chicago for just one trip.
Hopefully, this list has helped you pick the best Chicago rental for you, from bougie lofts fit for royalty to budget-friendly homestays. There's a Chicago rental to suit each and every travel style.
The only thing left is to secure it. Book your Chicago trip today and see why a short-term rental is so much better than a stuffy hotel room.
Some of the best Chicago rentals might even give you a similar view.
