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Apartment vacation rentals in Downtown Chicago

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Top-rated apartment rentals in Downtown Chicago

Guests agree: these apartments are highly rated for location, cleanliness, and more.

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A modern kitchen area features a wooden accent bar with four metal stools. Stainless steel appliances, including a refrigerator and stove, are visible. A wall clock adds a functional element to the open concept design, with neutral tones enhancing the spacious ambiance.

Apartment in Park Ridge

4.78 out of 5 average rating, 463 reviews

Modern Garden apartment (WHOLE UNIT)

Freshly Remodeled , Lower Level Condo one bedroom one bath. The Condo is very large for a one bedroom. Very Spacious with its open concept layout. Parking is right next to the main entrance of the building. Perfect place to relax Perfect and safe place to rest . 24/7 perimeter monitoring cameras. The Condo is very close to the Metra Train. It is !5 min away from O'Hare airport and 10 min from Chicago outlets etc. It is not a party room . No parties or large gathering .... Garden Apartment

A spacious living area is furnished with a dark sectional sofa, accented by decorative pillows. A round coffee table rests on an area rug, while a television is placed on a dark wooden stand. Natural light filters through large windows with sheer curtains.

Apartment in Chicago

4.98 out of 5 average rating, 210 reviews

Chicago Airbnb Newly Remodeled 2-Unit Apartment!

Enjoy Chicago in style! This newly renovated apartment on Chicago’s west side offers high end finishes and all of your basic needs. This unit features 2 spacious bedrooms and one bath with a jetted soaking tub so that you can unwind after a long day of exploring our beautiful city. Commuting around the city from this location is super easy! You’re only one block away from the CTA blue line train, CTA #7 Harrison Bus and I-290! The train and interstate can get you downtown in just 15 minutes!

A comfortable living area features a white sofa paired with a wooden coffee table. Soft lighting highlights a patterned area rug, while large, sheer curtains frame a bright window. A trellis of greenery decorates one wall, adding an element of nature to the space.

Apartment in Chicago

4.96 out of 5 average rating, 144 reviews

COZY Bright*BOLD*FUN* Eclectic Wicker Park Home

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit. Bright top floor unit with a private patio to just chill and unwind or walk downstairs and your literally in the heart of Wicker Park. Super easy access to downtown nightlife/lake/museum all within 15 minutes and super easy commute to O'hare. CTA busses all around and a 2 minute walk to the Blue Line.

An open-concept living area features large windows that allow natural light to fill the space. A comfortable couch is paired with a stylish armchair, and a minimalistic coffee table sits on a soft area rug. A flat-screen TV is mounted on the wall, complementing the modern décor.

Apartment in Chicago

4.94 out of 5 average rating, 103 reviews

Clean, Bright Chicago Apt in Bucktown/Logan Square

The whole group will enjoy easy access to everything from this centrally located place. The Western Blue line stop that takes you to downtown Chicago is 2 blocks away. Downtown is a 15 minute ride away if you decide to rent a car. This is the only apartment in the building and sits right above the BEST Grilled Chicken restaurant in Chicago. The apartment is walking distance to many delicious restaurants and local coffee shops. You can find some of the best food in Chicago just steps away.

The kitchen includes modern appliances, white cabinetry, and a tiled floor. A view into the adjoining living area reveals a comfortable seating arrangement. Natural light enters through a nearby window, enhancing the functional kitchen space.

Apartment in Chicago

4.86 out of 5 average rating, 542 reviews

Logan Square Lookout

Great 1st floor apartment along a tree lined street with free street parking. Has 2 cozy bedrooms with a spacious living room and kitchen. On site laundry. Great back yard with garden area. In the super nice Logan Square neighborhood with cool bars and award winning restaurants. Friendly safe neighborhood with lots to do. Quick walk to the Blue Line gets you Downtown or out to O'Hare. I own the building which consists of 3 apartments. So always nearby. permit parking is provided

A cozy living area is presented with natural light filtering through the wooden blinds. A light-toned sofa with patterned cushions faces a wooden coffee table, accompanied by a flat-screen TV. Colorful area rugs and a potted plant add warmth to the space.

Apartment in Chicago

4.88 out of 5 average rating, 138 reviews

Sounds Of The City

Fun and lively location! Cozy one-bedroom "stumbling distance" from McGee's Tavern and Grille, as in right upstairs. It’s pretty peaceful during the day except some train noise but the popular bar below ranges from a little noisy to pretty loud at night. Lincoln Park is an upscale, safe & convenient area. Walking distance to cafes, dining, pubs, parks, transportation, Lyft bikes, yoga, fitness, Amazon, etc. Weekends draw the biggest crowds and noise. Free street parking.Easy Uber/Lyft

A cozy living area features a gray sectional sofa positioned across from a light coffee table. A tall indoor plant adds a touch of greenery, while natural light filters through the window, adorned with sheer curtains. A dining area is visible in the background.

Apartment in Chicago

4.82 out of 5 average rating, 116 reviews

Chic Penthouse In Perfect Wrigleyville Location

Bright and open top floor apartment within easy walking distance to many of the best sites in Chicago: Wrigley Field, Lake Michigan, Lincoln Park, top notch neighborhood restaurants, pubs, and entertainment, and many more! With so much to do in the area and easy access to public transit you're sure to have jam-packed days of exploring and enjoying the city. After a long day, come back to this peaceful apartment to relax, recharge, and prepare to do it all again tomorrow. Book today!

A spacious living area features a large sectional couch complemented by decorative pillows. A white coffee table sits centrally on a plush area rug. An elegant armchair with a high back is positioned near a large window, allowing natural light to brighten the room.

Apartment in Chicago

4.84 out of 5 average rating, 817 reviews

Hip Chicago Apartment - FREE Parking Spot Included

You’ll love this high-end, newly renovated 2 bedroom apartment located in Chicago’s iconic Logan Square. This bright and modern space has free parking, a fully equipped stainless-steel kitchen and an outdoor sitting area perfect for a sunny meal. Walking distance from a bike rental station and hip Armitage Street where you can find a wide selection of restaurants and bars to suit any palate. You’ll also be close by the 606 Trail, a lovely place to enjoy a walk, bike or go for a run

A spacious living area features a large, cozy couch with warm, muted tones. A round black coffee table sits in front of the couch, adorned with a vase of fresh tulips. Natural light enters through two windows, with simple gray curtains providing a soft accent.

Apartment in Chicago

4.82 out of 5 average rating, 103 reviews

Bucktown Garden Suite 7 min walk to train

Bucktown Garden Apartment in A+ location on quiet neighborhood street. Private suite equipped with full bath, fridge, snacks, large couch, and queen-sized bed + free public laundry with soap provided. Walk in any direction to get to some of Chicago's best bars and restaurants or hop on the blueline subway 3 blocks away and zip downtown to explore some tourist attractions. Very easy, free street parking on the block. NO SMOKING/VAPING OR DRUG USE ON THE PROPERTY

A cozy living space features a round table with two woven chairs and a small potted plant in the center. A light-colored sofa is placed against the wall, accompanied by a floor lamp on a side table, creating a comfortable atmosphere.

Apartment in Whiting

4.84 out of 5 average rating, 163 reviews

NEW! |Studio Apartment Whiting IN, United States#2

Welcome to the Charming town of Whiting! The charming town of Whiting is located on the southern shore of Lake Michigan. Whiting is neighbor to Hammond IN & Chicago IL. This space is only 2 minutes away from the skyway with easy access to the city of Chicago & only two blocks down from the Hammond Horseshoe Casino. These newly renovated units also offer a comfortable and convenient stay for those who would like to travel and explore both cities.

Top guest favorite

A comfortable seating area features a wooden sofa adorned with checkered cushions. A coffee table sits in front, while a light fixture mounted on the wall adds illumination. A large artwork depicting a cityscape with the Eiffel Tower is displayed above the sofa.

Apartment in Evanston

4.97 out of 5 average rating, 108 reviews

Charming one bedroom apartment

Downtown Evanston. Cozy quiet area. Lovely studio 1-bedroom apartment. Ideal for a couple or business travelers. One queen size bed. TV & WiFi, microwave, AC & dishwasher. Free off-street parking. Close walk to Northwestern U, Lake Michigan, several supermarkets & many restaurants. Minutes to Metra, Davis & Dempster CTA stations. About 40 minutes to downtown Chicago on CTA Purple Express & less time on Metra. Non-smoking.

A spacious living area features a cream-colored sofa near a large mirror. A round dining table with four chairs is set in the center, accompanied by a wooden desk and a lamp. Natural light flows in through the window, illuminating the light decor.

Apartment in Evanston

4.83 out of 5 average rating, 178 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5 ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!

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What guests are saying

Beautiful Big 3 bedroom Quiet Apt near downtown

4.75 out of 5 average rating, 12 reviews4 months ago

The space is on the 3rd floor of a nice brownstone, Bianca was very responsive. The beds are all pretty comfortable! Big plus in a short term rental. The only things that could be better was, the thermostat had a lock box on it so we were unable to adjust that. There was a Keurig coffee maker but no k-cups or coffee. We were there for 2 nights and would come back.

Apartment in Chicago

What guests are saying

1 Bedroom Apartment/free parking

4.86 out of 5 average rating, 28 reviews1 month ago

We stayed at Karolinas apartment for 7 months and she was a wonderful host. She quickly addressed any problems. For example, we locked our keys in the apartment. I texted her and a new set of keys were promptly delivered. The apartment itself is super comfortable. Great furniture and appliances and we enjoyed the outdoor balcony. I would highly recommend renting from Karolina and this apartment specifically. We have no complaints and our stay was wonderful. Thank you Karolina!

Apartment in Glenview

What guests are saying

Beautiful, sunny 2nd floor 3BR/1BA w free parking

4.93 out of 5 average rating, 124 reviews1 week ago

Chad and Jodees place was great for us and our 5 and 2 year old. They had lots of kid friendly amenities like toys, plastic dishes, and books. It’s also walkable to a large park. We had a minor issue with the toilet and Chad came up immediately to fix it (they live right downstairs). The apartment makes very efficient use of space and had everything we needed for 5 days in Chicago.

Apartment in Chicago

What guests are saying

Executive Apartment on Lake Michigan with parking

4.89 out of 5 average rating, 166 reviews1 month ago

This was a beautiful place with an excellent view of Lake Michigan. Both rooms had comfortable beds and setup with everything you need. Kitchen is well stocked, but we mostly ordered Grub Hub, lol. Loved spending time here and great place to hangout and chat with friends. It is right on the water and we really enjoyed watching the waves crash against the barrier. It is on the 2nd floor, but the stairs are not bad at all. Felt very safe and having the parking space is a great perk. Very commutative and checked in with us to make sure everything was fine. Would definitely stay here again!

Apartment in Chicago

What guests are saying

Superb 2BR Old Town APT, PRIME LOCATION!(+Parking)

4.78 out of 5 average rating, 292 reviews1 week ago

This is a great spot to stay in Chicago, the location really couldn’t be much better. Easy walk to red line which gets you everywhere you need to go, and it being a one way street keeps traffic low in comparison. That being said it’s not an alley or a sketchy area by any means. Walk right out 30 yards to your left to a good view of the Willis tower and lower skyline, or walk to your right for great shopping and restaurants in old town. It couldn’t be better. The place is nice, does get a bit chilly at night which is honestly ideal for sleeping, you will be sharing the one bathroom if you have multiple guests but with me and my family it worked fine. Thanks Nicole and Matt for a great stay on spring break with the kids!

Apartment in Chicago

What guests are saying

West Town Modern Garden 1

4.78 out of 5 average rating, 55 reviews3 weeks ago

My sister and I had a great stay at Julian's listing. The home was clean, comfortable, and felt safe. The location offered great access to public transportation and plenty of nearby restaurants. Plus, it's just a short ride from downtown, making it easy to explore the city every day.

Apartment in Chicago

What guests are saying

Skylights, King Bed, 2 bedrooms

4.92 out of 5 average rating, 251 reviews3 months ago

it was a very good stay the place was exactly as described and the beds were very comfortable! The only comment I would have was regarding the staircase getting into the apartment which was very narrow and difficult to drag suitcases up! While this was not really an issue for us I would suggest mentioning it in your listing so that in case elderly people come they know what to expect. Overall great stay!

Apartment in Chicago

What guests are saying

Top Notch 2 Bedroom Apt. close to Downtown Chicago

4.78 out of 5 average rating, 94 reviews5 months ago

The communication with Naj was efficient and cordial. He made himself available and responsive. While we didn't need to talk much (the place was clean and well represented in the photos), we appreciated his care and approachability. The place is quite close to a train line and the neighborhood felt safe!

Apartment in Chicago

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Popular amenities for Downtown Chicago apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

A modern living area features a gray sofa facing a round marble coffee table. Behind, a built-in bookshelf holds various books. Natural light streams through multiple windows, illuminating a dining area with a round table and stylish chairs. Greenery adds a touch of nature.

Apartment in Chicago

4.95 out of 5 average rating, 111 reviews

Chic retreat near the best of Lakeview & Wrigley

A light and airy living area is furnished with a gray sofa and two comfortable armchairs. A round coffee table rests on a patterned area rug, with a window allowing natural light to fill the space. Simple decor adds a touch of warmth.

Apartment in Chicago

4.94 out of 5 average rating, 105 reviews

Bright two bedroom garden apartment

A spacious living area features a fireplace with a decorative mantle and a large television. Two bright red armchairs are positioned across from a modern coffee table. Light streams in through windows, illuminating the hardwood flooring and surrounding decor.

Apartment in Chicago

4.91 out of 5 average rating, 193 reviews

Comfortable Vintage North Side Retreat for 8

Top guest favorite

A spacious living area features a vibrant area rug with geometric patterns, complemented by a teal sectional couch and circular ottoman. A modern armchair and side table provide additional seating. Natural light flows in through large windows, and indoor plants add a touch of greenery.

Apartment in Chicago

4.98 out of 5 average rating, 101 reviews

Vibrant Lg Chicago 2BR Close 2 Everything & Nature

A modern living room features a plush sectional sofa adorned with decorative pillows. Two framed monochrome artworks are displayed on the wall above. A round coffee table sits in front, complemented by a small potted plant and a stylish floor lamp providing ambient light.

Apartment in Chicago

4.94 out of 5 average rating, 237 reviews

Cool and Modern Chicago Apartment near Transit

A fully equipped kitchen features modern appliances, including a stainless steel refrigerator and microwave. A large island with two metal stools offers additional seating. Natural light streams in through the window near the sink, illuminating the sleek countertops and cabinetry.

Apartment in Chicago

4.85 out of 5 average rating, 161 reviews

*Comfortable & Spacious Home Close to Downtown*

Apartment in Chicago

4.85 out of 5 average rating, 171 reviews

Oasis Collection's Mid-Century 3 Bd Wicker Park.

A modern living area features a light-colored sofa adorned with decorative pillows. A small coffee table sits at the center, complemented by a decorative globe and a plant. Two windows allow natural light, while a mirror and dining area are visible in the background.

Apartment in Chicago

4.83 out of 5 average rating, 262 reviews

BERNARD CHATEAU - LOGAN SQUARE

Private apartment rentals

An open-concept living area features a light-colored sofa with coral throw pillows, positioned around a modern white coffee table. A sleek kitchen is visible in the background, highlighted by pendant lighting and stainless steel appliances. A decorative plant adds a touch of greenery to the space.

Apartment in Chicago

4.91 out of 5 average rating, 135 reviews

Modern 3BR with Private Rooftop & Free Parking

A cozy living area is visible at the end of a corridor, featuring a light-colored sofa atop a neutral-toned rug. The walls are lined with wooden paneling, and a piece of artwork is mounted to the wall, enhancing the warm atmosphere.

Apartment in Chicago

4.9 out of 5 average rating, 144 reviews

Private Garden Apartment GATED FREE Parking

A modern living space features a dark sofa adorned with colorful cushions. A round coffee table sits in front, accompanied by a small side table with a decorative vase. A large mirror reflects the cozy atmosphere, while a vibrant city skyline artwork adds visual interest to the wall.

Apartment in Chicago

4.97 out of 5 average rating, 106 reviews

Lovely 2bedroom 1bath Apt and outdoor seating.

Top guest favorite

A comfortable seating area is presented with a sectional sofa and a green armchair. A glass coffee table is centered on a soft area rug, enhancing the space's warmth. Two framed artworks are displayed on the light gray walls, complemented by natural light filtering through a window.

Apartment in Chicago

4.92 out of 5 average rating, 276 reviews

Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby

A tastefully arranged living area is highlighted by a decorative fireplace and stylish furniture. Two sofas flank a round coffee table, while light streams through tall windows. A delicate floral arrangement stands on the mantel, and a gold chandelier adds elegance to the space.

Apartment in Chicago

4.76 out of 5 average rating, 259 reviews

North Side Pied-à-terre

Apartment in Evanston

4.85 out of 5 average rating, 248 reviews

Adorable 1BR apartment near Northwestern

A modern living area features a beige sectional sofa and a round coffee table set on a patterned rug. A large flat-screen TV is mounted on the wall, and a potted plant adds a touch of greenery. Natural light illuminates the space.

Apartment in Chicago

4.83 out of 5 average rating, 184 reviews

New apartment

A stylish corner features a modern arc floor lamp casting warm light. A small side table with a turquoise surface is accompanied by two coasters. Nearby, a patterned throw pillow rests on a textured accent chair, complementing the minimalist artwork on the wall.

Apartment in Chicago

4.88 out of 5 average rating, 282 reviews

Stylish & Modern 2 Bedroom Lincoln Square Condo

Apartment rentals with a hot tub

An open living area is displayed with floor-to-ceiling windows offering city views. A sleek sofa and two stylish chairs are arranged on a patterned area rug. A wooden dining table is visible next to the windows, enhancing the spacious atmosphere of the penthouse.

Apartment in Chicago

4.85 out of 5 average rating, 89 reviews

Quiet but in the Heart of City walk Everywhere

A bright living area features large windows offering city views. A dark gray sofa and armchair frame a round coffee table, complemented by a light area rug. A dining table for two is positioned near the window, with a gallery of artwork on the walls enhancing the ambiance.

Apartment in Chicago

4.9 out of 5 average rating, 42 reviews

The Areal Oasis

The image shows a collage of the unit's features. The upper left showcases a spacious living area with light-colored furnishings and large windows. The upper right displays a comfortable bedroom with a neatly made bed and minimal decor. The bottom left features a fully equipped kitchen with wooden cabinets and modern appliances. The bottom right highlights a game area with a dartboard and a game table.

Apartment in Chicago

4.57 out of 5 average rating, 7 reviews

Minutes to Wrigley Amazing Location - Sleeps 6

A bright and airy living area is filled with natural light from floor-to-ceiling windows, offering expansive city views. A plush sectional sofa is positioned on a soft area rug. Potted plants and a console with a television add to the inviting ambiance.

Apartment in Chicago

4.96 out of 5 average rating, 24 reviews

Skyline Oasis: City & Lake Views

A private hot tub is set on a rooftop deck, featuring bubbling water and a city skyline backdrop. Plush seating with soft cushions is arranged nearby, creating a comfortable space for relaxation. The view includes various high-rise buildings against a colorful sky.

Apartment in Chicago

4.85 out of 5 average rating, 53 reviews

Rooftop HotTub As Seen On "Married At First Sight"

A living area features two sofas and a coffee table centered on a colorful area rug. Warm lighting emanates from two table lamps beside the sofas. Artwork adorns the wall, enhancing the cozy ambiance of the space.

Apartment in Chicago

4.82 out of 5 average rating, 11 reviews

Large Studio Apartment with no cleaning fee

Top guest favorite

The open-concept living area features a comfortable green sofa, stylish coffee table, and wooden dining table with four chairs. Modern kitchen appliances are visible in the background, accompanied by wooden cabinetry. Natural light illuminates the space, creating a welcoming environment.

Apartment in Chicago

5 out of 5 average rating, 6 reviews

Luxurious 3BD Penthouse- Private Patio+Gym+Rooftop

Top guest favorite

A hot tub is positioned in a vibrant game room, surrounded by colorful murals depicting a beach and lively graphics. Water glistens in the tub, inviting relaxation and enjoyment after a day of activities.

Apartment in Chicago

4.98 out of 5 average rating, 104 reviews

Belmont Pleasures - hot tub / arcade gaming room

Destinations to explore