Apartment vacation rentals in Cook County

Plants and Art | Near Trendy Restaurants & Bars

Light-Filled Apartment Near Chicago’s Best Restaurants & Bars • Friends & Couples • A/C • Coffee Station w/Local Beans • Fully-Equipped Kitchen Whether you’re in town to explore or unwind, you’ll love the proximity to restaurants, cafes, and live music venues - the perfect home base for your Chicago adventure. Extra Fees: *only available upon request and approval* Early Check In@ 2pm : $50 @10am:$100 Late Checkout@ 1pm: $50 @9pm:$100 Shipping: $25 + UPS fees Required for 7+ Days: $80 Cleanin

Hidden Gem:Artsy Speakeasy in Historic Bronzeville

Enjoy this fun and unique 1-bed 1.5-bath speakeasy in the heart of Chicago's Bronzeville District. This artsy vibe features eclectic décor, hand-painted murals, Smart TVs, wet bar, wellness studio, remote workspace, free street parking, and ground-level-step-free access. This cozy space is perfect for fun couples, solo adventurers, business travelers, and game night aficionados. Easy access to Downtown (6 miles to Mag Mile, Navy Pier, Millennium Park), Beach (1 mile), Museums, & Sports arenas.

City-Accessible Basement Retreat

Discover a perfect mix of small-town charm and city life in this cozy basement unit. Situated just a 7-minute walk from the train station, downtown Chicago is easily accessible for work/leisure. The neighborhood is a treasure trove of local restaurants, bars, and stores, ensuring you're never far from what you need. A convenient gas station/store is right behind your home for quick needs. Ideal for a simple, connected lifestyle with the city’s pulse at your doorstep. Your urban retreat awaits!

Rockin' 2Bed steps to shops/food/train

This musically-inspired vintage 2 BR is perfectly placed in Oak Park and we know you'll have a rockin' vacation here. Steps to shops, cafes, train, and FL Wright home. With a cassette wall, reading nook, and many other cute touches. The apartment is a vintage brownstone with charming details, like original woodwork. Street parking available. Easy access to Chicago.The place is an older Chicago brownstone, with a lived-in feel. NO PARTIES!! Upstairs neighbors can be heard walking and moving

Private City Hideaway

Park in the private garage and walk to restaurants, coffee, bars , cafes and shopping. 10 minutes to the train! All outside your front door from this entirely private extra large one bedroom city apartment. Well appointed kitchen, free laundry, wi-fi, heat and air cond. No parking worries with included garage parking!! Click SHOW MORE - for detailed location information - Click SHOW MORE Wrigley Field 8 minutes Uber 15 public transport 30 walking NOTE: no smokers no visitors

Fully Furnished Apartment Wicker Park Free Parking

Hello and welcome to all seeking a comfortable and convenient place to stay in Chicago! Please enjoy your time away from home in our fully furnished apartment located in the trendy neighborhood of Wicker Park! Please view the list below of all the wonderful amenities we offer to every guest staying out apartment. Again if you have any questions or comments please do not hesitate to ask. I look forward to seeing you and having your apartment ready soon! Thank you! One night available

Cozy guest studio, great for couples!

This unique place has a style all its own. Enjoy this beautiful, cozy guest studio with modern touches and well furnished living area, small kitchenette with mini fridge and microwave to reheat a quick bite before heading to the city, full bathroom with rainfall shower and handheld sprayer to help you relax after a long day. Flat screen TV with Xfinity streaming device so you can connect your accounts and enjoy your favorite shows and movies for a quiet stay in.

Modern Apt with style & comfort in Pilsen Chicago

Enjoy a nicely updated studio in a safe, family-owned building located in Pilsen/Heart of Chicago conveniently located near Downtown, Chinatown, & Hyde Park to name a few. Public transportation is walking distance or you can go on a short drive to museums, parks, cafes, restaurants, bars, venues, and hip neighborhoods. Chicago has a full line up of festivals happening this year so feel confident in choosing my lovely space to be part of your experience.

Quirky Quarters at Wrigley

I think you are just going to love my apartment. The space features wonderful large street level windows in the living room and has all of the quirky charm that vintage buildings offer up. The location literally can't be beat, with the apartment a ten minute walk from Wrigley Field, the bustling Southport shopping corridor, and both the red line and brown line subway stations. There is no parking available with the apartment.