Holiday rentals with outdoor seating near Shedd Aquarium

Bright 2Bed 2Bath in Brand New Pilsen Development

Experience upscale city living with @TheDreamRentals in this stylish 2-bedroom, 2-bath Airbnb located in Chicago’s vibrant Tri-Taylor neighborhood. This modern retreat features sleek interiors, spacious bedrooms with queen beds, a fully equipped gourmet kitchen, and designer finishes throughout. Enjoy high ceilings, large windows, and smart amenities just minutes from downtown, the United Center, and the Illinois Medical District. Perfect for professionals, couples, or small groups seeking com

The Executive's Escape (2BD / 2BA)

Located at the epicenter of Chicago's cultural, historical, and business attractions, this luxurious 2 bedroom apartment offers guests all the comforts of home, whether on the road for work or play. Within walking distance are world famous attractions including: Millennium Park, The Bean, Navy Pier, Riverwalk, Soldier Field, The Field Museum, and more. Additionally, guests are merely a couple blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city.

South Loop 2BR Oasis w/ Patio, Gym Near Navy Pier

Welcome to your urban escape in the heart of Chicago's vibrant South Loop neighborhood! This stylish 2-bedroom, 2-bathroom suite is thoughtfully designed to provide a perfect mix of comfort, convenience, and elegance for business travelers, families, and tourists alike. Whether you're here for a conference at McCormick Place, a fun weekend in the city, or just looking for a relaxing getaway, we're just steps away from iconic Chicago attractions and offer optional on-site parking for convenience

Comfy and Walkable

You will be close to everything when you stay at this comfortable apartment that is close to everything but quiet and friendly. This is my home. I travel a lot and airbnb it when I'm away. It's comfortable, safe, has all the things a lived-in home has, and is in an amazing location. It's like staying at your friend's apartment in the city. If you want luxury, pay more and stay somewhere else... but this is exactly the kind of place I'm looking for when I travel and I hope you'll enjoy it too!

Retro Modern Bungalow | fire pit | free parking

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Entirely Private Suite - Urban Oasis - Pilsen/UIC

Pilsen - McCormick Place - Soldier Field - Thalia Hall - UIC - Chinatown - South Loop - Radius Welcome to a brand new, entirely private, spacious and peaceful oasis in Pilsen-UIC with a smartlock system and self check in. Central location near some of the hottest neighborhoods, restaurants, concert and tourism venues, and minutes from the Loop! Full bath with a luxurious spa shower, cable, wifi, flatscreen tv, refrigerator, iron, desk, coffeemaker, toiletries and a lovely private deck.

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

Bright & Spacious| Free Parking |Trendy Bridgeport

Step inside and be greeted by an open-concept space bathed in natural light. High ceilings, hardwood floors perfectly blend vintage charm with modern elegance. The living area invites you to unwind after a day of exploring our vibrant city. Relax on the sofa, watch your favorite shows on our large flat-screen TV, or indulge in book in the cozy seating nook. Whether you're a solo traveler, couple, or friend group looking for an unforgettable adventure, this is the ultimate urban retreat.

The Green Bungalow: Charming 1-BR apt. with patio

Situated in a residential neighborhood just outside the city limits, this lovely 2nd floor apartment is blocks from the Blue Line train and highway. Our newly renovated vintage unit has a full kitchen, hardwood floors, plenty of natural light, a backyard patio and its own private entrance. Our bungalow is walking distance to cafes, restaurants, shopping, music and nightlife. Enjoy the charm of the suburbs while having easy access to all the attractions Chicago's downtown has to offer.