Holiday rentals with beach access in Downtown Chicago

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 TV, 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), Navy Pier, Obama Library, Millennium Park, Beach (1 mile), Museum, & Sports arenas.

The Lakefront Lookout (Rooftop Deck • Gym)

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, Navy Pier, Riverwalk, Soldier Field, The Field Museum, Oak Street Beach, and more. Additionally, guests are merely blocks from an "L" train stop, which will transport passengers anywhere they could desire in the city!

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

Evanston 2BR 2Bth 1 Blk to Beach

With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

Quiet city getaway by beach in fun neighborhood

Welcome to this bright and modern 2 bedroom 1 bath getaway, 1.5 blocks to Andersonville + Uptown shops and dining. Located on a quiet tree-lined street walking distance to Foster beach, grocery, concerts, and CTA for easy access downtown. Two bikes provided to explore Chicago’s neighborhoods and beautiful lakefront path. Additional amenities include beach towels, volleyball, cooler, free on-site w/d and parking. Comfortably sleeps 4 and can accommodate 6 with air mattress. Key code entry.

2BD/2BA MAG MILE MASTERPIECE (+Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Tranquil rooftop overlooking the Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows We look forward to hosting you!

Modern MAG Mile 2BD/2BA (+Parking/Rooftop)

Welcome! Guests love our home because: - You're SECONDS from the LAKE and MAGNIFICENT MILE - You're steps away from the famous Drake Hotel and Oak Street Beach. - Walk to every popular attraction that makes Chicago so great! - Newly remodeled interior with an open floor plan layout - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

Gold Coast Pristine 3BD|2BR| Patio |Parking| Beach

FREE GARAGE PARKING! Garage Clearance 6ft. Step into luxury in this modern loft with 3 bedrooms, 2 bathrooms and a private patio with breathtaking views. Experience the feeling of being at home in a bright and spacious haven amidst Chicago's most sought-after neighborhood "Gold Coast" This centrally located gem is situated within walking distance of much of Chicago Downtown's exquisite dining, upscale boutiques, popular tourist destinations, and just a stone throw away from Oak Beach.

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

Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations steps from world-class shopping and restaurants, Oak St. beach, and public transportation (L trains, express bus). Includes A/C, washer-dryer, super-fast wi-fi, smart TV, and workspace. Hourly rate garage parking next door. Note: Guests must walk up two flights of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

Blue Brick Apartment in Bridgeport - Park for Free

• Free street parking • Trains to Downtown!! • Fully stocked kitchen • Walk to dining & bars! • Free parking pad in rear • Noise monitoring equipment • Walk score 93! Bike Score 92! • 600 sq ft apartment | 2nd floor | Patio • Safe, working class neighborhood! • Commute to Downtown: 15min (drive) • 28min (transit/train) | 22min(bike) • Building video surveillance alarm system • Washer | Dryer | Dishwasher are included • Rideshare (Uber/Lyft) | Bikeshares(Divvy)

Stylish 2BR Andersonville — Walk to Lake & Cafés

Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.

Spacious and Newly Renovated 1BR Next to the Beach

1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building. Enjoy our cozy 1BR/1BA apartment near Lake Michigan in Evanston. Features a fully equipped kitchen, a comfortable bedroom with a queen bed, and a clean bathroom. Walk to beaches, the lakefront, and vibrant downtown with shops and restaurants. Easy public transit to downtown Chicago. Book now for a memorable stay!