Vacation rentals in Chicago River

A+Chicago Roscoe Village Entire Home Wrigley+ More

Elegant large bright posh eclectic flat in heart of Roscoe Village very comfortably furnished to enjoy charismatic Chicago. Free parking. Very fast internet and laptop comfortable space for your home office. Professionally cleaned, well appointed cozy, perfect for families or a solo traveler. Fab decor, fully stocked kitchen plus all amenities and an open-plan layout invites you to enjoy quiet elegant comfort of home. Easy walk to Wrigley Field. Take the bus or train downtown. Easy walk to wine & dine in posh areas of Roscoe Village, Lake view & Lincoln Square. Or a quick drive to downtown! This is A FULL UPPER FLOOR, and NOT a Garden Basement. You are a short walk away from restaurants, stores but stay in a quiet beautifully appointed 1100 square feet elegant 1 large Bedroom flat with parking all to yourself. Enjoy this -its hard to find in this city. Refurbished to the highest standards this spacious apartment is located moments from shopping, restaurants and pubs in the heart of cool Roscoe Village Lakeview & Lincoln square neighborhoods of Chicago. Famously eclectic and vibrant, we are the heart of Chicago's best offerings. Boyztown, Buck town, Lincoln park or music at Scubas, Stage 777, Revolution Brewery, and other cool hip spots are a short walk or ride away. Home of the CUBS -Chicago’s best attractions "Walking to Wrigley field with all of the other "fans" singing GO CUBS was a fab experience" a guest's comment. The most difficult decision of the day might well be whether to eat out - many restaurants, pubs and bars in the area catering for all tastes and pockets; or to stay in and cook - cozy comfort of a first class home. We are keen for you to enjoy your stay with us, and we will do our best to make your stay a memorable one. The accommodation is the whole upper floor, (one short flight of stairs) and you have your own entrance. Enjoy a luxurious home away from home. You have an entire floor to yourself with 100% privacy. Interaction with our guest is as much or as little as you need, when we are in town. We often travel, but always have a caretaker who will be responsible to ensure satisfaction for your complete stay. Part of the area's charm is not only the elegant vintage Chicago style homes, or how easy it is to walk to all the local favorite dining, but how much personality all the small independent businesses on Roscoe street have. This gives the neighborhood a hip vibe and friendly, small-town feel! Centrally located in the middle of Wrigleville, Lakeview, Bucktown, Logan Square, Lincoln Square and 10 minutes to train station - 5 minutes to bus or divvy bikes. Or park your car FREE - a luxury in Chicago Centrally located, yet quiet and charming you will be within minutes of everything this mega city has to offer. Chicago is a major city second only to New York, in the United States, and is a global alpha city with fantastic offerings. This glittering city built on the shores of Lake Michigan is where you’ll find some of the biggest and best entertainment outside of New York City and Las Vegas, including touring Broadway shows, professional sports teams, stand-up comedy and concert venues – including the iconic Chicago Theater and Grant Park, home of Lollapalooza. The second city is also home to year-round attractions and world-class museums – the Field Museum, the Skydeck at the Willis Tower, Shedd Aquarium, and the Art Institute of Chicago. Chicago sports fans fuel their passion year-round as they cheer on the north side Cubs or south side White Sox in the summer, Bulls and Blackhawks in the winter, and Bears in the fall.

LIVN Millennium Park Downtown Chicago 1 BR

Experience the best of Chicago from this stylish, newly renovated 1-bedroom at 19 S Wabash Ave. Perfectly located in the heart of downtown, you'll be steps away from iconic Millennium Park, the vibrant shops of Michigan Avenue, and a world of dining options. This 1 bedroom offers modern comfort with a fully equipped kitchen, including a refrigerator, dishwasher, and coffee maker, plus the convenience of an in-unit washer and dryer, making it ideal for both short getaways and extended stays. Enjo

Location! HUGE Wicker Park Concrete Jungle ROAR

Location! Location! Location! Prime Wicker Park Location on Milwaukee! This HUGE bright second floor unit is very spacious, cool, vibrant, eclectic, fully equipped apartment is close to everything, making it easy to plan your visit to 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.hole group will enjoy easy access to everything from this centrally located place.

3-bedroom exposed brick in Chicago's Wicker Park

Welcome to Wicker Park - one of Chicago's coolest walkable neighborhoods with endless restaurants, bars & shops. 2 blocks from the famous "L" train with access to the city & O'Hare airport. This 1893 vintage apartment has been freshly renovated and professionally designed blending historic details with a clean and modern aesthetic. The instagrammable one of a kind space has beautiful hardwood floors, soaring 10ft ceilings, exposed brick in all rooms, curated decor and a cozy private deck.

Spectacular 2BR Penthouse in the Loop | Roof Deck

This top floor corner penthouse is in a perfect location with panoramic city views in multiple directions. With over 1,200 square feet of space, 13 foot tall ceilings and oversized windows, this spacious penthouse is a true escape in the sky in the heart of Chicago. It's a two bedroom, two bathroom apartment with an additional sofa bed. The building has a pool and an amazing outdoor rooftop terrace with 360 degree views of the skyline and lake. This is the best location in the city!

Kasa | Views from your Private Balcony | Chicago

When you're in Kasa Magnificent Mile, the city is yours for the taking. Our prime location makes exploring Chicago easy. Located just north of downtown Chicago, you'll be steps from Oak Street Beach, a short walk to Michigan Avenue and Millennium Park. With fantastic amenities, our apartments are ideal for extended stays or long vacations. Our tech-enabled apartments offer self check-in at 4pm, 24/7 guest support by text or phone, and a Virtual Front Desk accessed via mobile device.

Lovely 1-bedroom serviced apartment near Museums!

Enjoy Chicago in our modern & spacious 1-bedroom loft in the South Loop. Central location to Grant Park, Soldier Field, Museum Campus, McCormick Place and more! Our location has a walk & transit score of 97, providing easy access to all the hot spots on your itinerary! Expect lovely natural light, luxuriously tall ceilings and room to accommodate your entire group. Guests are always pleasantly surprised by the size of the space and the modern amenities we provide!

Urban Chic Apartment by the Magnificent Mile

Ideally located just half a block from Michigan Avenue, this bright and open 3rd floor apartment boasts thoughtfully appointed rooms for your comfort so will have everything you need to enjoy your stay in style! PLEASE NOTE: 3rd floor walk up (NO ELEVATOR) There is a small neighborhood bar on the second floor of the building. They are respectful of our neighbors, however they do play music which can be heard in the living room but rarely in the bedrooms.

The Huron Haven

A beautiful, one-of-a-kind, hidden gem in the heart of River West. Private entry. Front & Back Patios. Full office space. Large Living Room. Exposed brick walls, 11.5’ tall ceilings. Large barn doors lead from the living room / office to a large master bedroom with large modern bathroom. The bedroom has French doors which open to private balcony with a beautiful back patio, dining space, and thriving garden. On Property Parking

Pilsen Modern Chic Retreat

Welcome to your perfect getaway! This stunning 2-bedroom home is the epitome of modern chic; offering an unforgettable blend of style and comfort. Designed for up to 6 guests, the space is crafted with thoughtful architectural details and an eye for eclectic decor. Located in the heart of Pilsen, known for its vibrant art scene, trendy restaurants, & local culture, you'll be perfectly situated to explore everything Chicago has to offer.

Elegant Suite in Gold Coast

Steps away from the Magnificent Mile, and the high-end boutiques of Oak and Rush Street, this generous one-bedroom apartment is perfectly situated in the middle of the action for your Chicago adventure. ***Please note that from March until the end of September 2026, there will be construction on the upper floors of the building that may cause noise during the daytime hours. Construction will not be happening on the weekends.***

Loop 1BR | Steps to Millennium Park & Bean

Steps from Millennium Park in downtown Chicago. Modern 1BR with queen bed, full kitchen, in-unit washer/dryer, WiFi, and workspace. Building offers heated pool, gym, and 24-hour concierge. Walk to The Bean (3min), Riverwalk (2min), Art Institute (5min). CTA Red Line across the street connects you everywhere. Perfect for couples or solo travelers seeking an unbeatable Loop location.