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Apartment vacation rentals in Chicago

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Top-rated apartment rentals in Chicago

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Rental unit in Park Ridge

4.79 out of 5 average rating, 390 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

Rental unit in Chicago

4.99 out of 5 average rating, 174 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!

Rental unit in Humboldt Park

4.82 out of 5 average rating, 107 reviews

Spaulding Oasis on 4 lots In Humboldt Park!

This first floor 2 bed room apartment has all the modern amenities you could want featuring central air and heat, glass shower door, high water pressure shower, for really getting clean! smart tv with all your streaming services plus local tv, back porch with table and chairs, recessed led lighting, ice maker, dish washer, stove with built in griddle, coffee and coffee maker, glass electric tea kettle, silverware, and all kitchen items found in a home, hard wood floors. With comfy couch bed !!

Rental unit in Wicker Park

4.96 out of 5 average rating, 126 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.

Rental unit in Jefferson Park

4.89 out of 5 average rating, 116 reviews

Modern 2 bdrm apt near O'hare and Downtown

Step into the vibrant Gladstone Park neighborhood, a mere mile from the blue line. Picture yourself minutes away from O'Hare airport, the Rosemont Convention Center, Fashion Outlet mall, and the thrilling Rosemont Casino. Your spacious haven awaits – a sunny 2-bedroom, 1-bath apartment, brimming with all essential amenities. Feel the convenience with in-unit washer and dryer, hassle-free parking on-site, and free street parking. Don't miss out – book your stay now for a colorful experience.

Rental unit in Lake View

4.82 out of 5 average rating, 123 reviews

Wrigleyville 4-Bed with Tons of Sunlight

The is a very comfortable spacious apartment with high ceilings, abundant sunlight. The kitchen and bath were recently remodeled. The location is the best of both worlds as it's nestled on a quiet side street surrounded by historic mansions yet is a quick walk to Wrigley Field, public transit, and the lake. Just a few short blocks to all the nightlife, shopping, arts/entertainment, and restaurants Wrigleyville has to offer. 20 minutes via EL train to Downtown, Mag Mile, Grant Park, etc.

Rental unit in Avondale

4.86 out of 5 average rating, 504 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

Rental unit in Logan Square

4.85 out of 5 average rating, 776 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

Rental unit in Whiting

4.84 out of 5 average rating, 134 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.

Rental unit in Lake View

4.92 out of 5 average rating, 184 reviews

Penthouse Near Wrigley Field

This beautifully furnished and spacious penthouse unit has tall windows and ceilings letting in loads of gorgeous light. It is perfectly located just a short walk to Wrigley Field, two train stations, and tons of bars and restaurants. (Just a 10 min train ride to Michigan Avenue!) FREE street parking and 24-hour check-in! Pet friendly- we allow one pet per reservation for a $100 non-refundable Pet Fee. Pet must be well mannered and under 60lbs.

Rental unit in Evanston

4.82 out of 5 average rating, 160 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/1.5ba 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!

Rental unit in Wrigleyville

4.93 out of 5 average rating, 341 reviews

Wrigleyville 75 yards from Wrigley Field

Beautifully remodeled apartment steps from Wrigley Field and bars. Half block from the field and One block away from the Wrigleyville night life. The apartment is right next to all the action but just far enough for a quiet night sleep. You will be pleasantly surprised how quiet my block is one hour after the game ends. Walking distance to the beach and a block from the red line.

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Popular amenities for Chicago apartment rentals

Free parking on premises

Air conditioning

Weekly apartment rentals

Rental unit in Lincoln Square

4.91 out of 5 average rating, 178 reviews

Comfortable Vintage North Side Retreat for 8

Rental unit in Lincoln Park

4.96 out of 5 average rating, 106 reviews

Elegant Depaul Apt on Jonquil Park

Rental unit in West Town

4.93 out of 5 average rating, 338 reviews

Spacious & private! Free parking! Great location!

Rental unit in Irving Park

4.93 out of 5 average rating, 226 reviews

Cool and Modern Chicago Apartment near Transit

Rental unit in West Town

4.85 out of 5 average rating, 161 reviews

*Comfortable & Spacious Home Close to Downtown*

Rental unit in Lincoln Park

4.75 out of 5 average rating, 197 reviews

Rare, Updated 1 BR Condo in Lincoln Park!

Rental unit in Logan Square

4.83 out of 5 average rating, 241 reviews

BERNARD CHATEAU - LOGAN SQUARE

Rental unit in Logan Square

4.9 out of 5 average rating, 162 reviews

Private 2 Bedroom Retreat

Private apartment rentals

Rental unit in Oak Park

4.87 out of 5 average rating, 268 reviews

Cosmopolitan Nest in Oak Park North Side

Rental unit in Near North Side

4.91 out of 5 average rating, 114 reviews

Modern 3BR with Private Rooftop & Free Parking

Rental unit in Lincoln Square

4.78 out of 5 average rating, 285 reviews

Cozy Garden-Subterranean Apartment

Rental unit in East Rogers Park

4.9 out of 5 average rating, 137 reviews

Private Garden Apartment GATED FREE Parking

Rental unit in Near North Side

4.98 out of 5 average rating, 208 reviews

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D

Rental unit in Avondale

4.91 out of 5 average rating, 255 reviews

Avondale Gem: 2BR, Stylish Kitchen, Transit Nearby

Rental unit in West Town

4.76 out of 5 average rating, 125 reviews

Wicker Park Historic, Art-Filled, Urban Oasis #2

Rental unit in Roscoe Village

4.75 out of 5 average rating, 246 reviews

North Side Pied-à-terre

Apartment rentals with a hot tub

Rental unit in Lake View

4.5 out of 5 average rating, 4 reviews

City Life, Neighborhood Comfort - Studio

Rental unit in West Rogers Park

4.87 out of 5 average rating, 47 reviews

Spacious Beautiful Condo

Rental unit in West Loop

5 out of 5 average rating, 19 reviews

Skyline Oasis: City & Lake Views

Rental unit in Chicago

4.85 out of 5 average rating, 53 reviews

Private Rooftop Views from Penthouse Suite

Rental unit in West Loop

4.83 out of 5 average rating, 12 reviews

Cloud9 | Co-Working+Golf @Fulton Market |The Retro

Rental unit in Magnificent Mile

4.87 out of 5 average rating, 93 reviews

4Br Gold Coast Duplex w Jacuzzi in the Bedroom!

Rental unit in Belmont Cragin

4.98 out of 5 average rating, 66 reviews

Belmont Pleasures - hot tub / arcade gaming room

Rental unit in Streeterville

5 out of 5 average rating, 20 reviews

Lake, City, & River View Condo

Quick stats about apartment rentals in Chicago

Total rentals
6.1K properties
Total number of reviews
291K reviews
Family-friendly rentals
2.9K properties are a good fit for families
Pet-friendly rentals
2K properties allow pets
Rentals with a pool
730 properties have a pool
Rentals with dedicated workspaces
4K properties have a dedicated workspace

Destinations to explore