Holiday rentals with beach access in Downtown Chicago

A modern living area features a spacious orange sofa and a wooden coffee table positioned on a light rug. A large flat-screen television is mounted on the wall, with a stylish lamp and potted plant nearby. An open kitchen with white cabinetry and stainless-steel appliances is visible in the background.

4.98 out of 5 average rating, 119 reviews

Bright & Modern Apt | Steps to Lake, Train, Food

This is the ideal location for your trip to Chicago! Steps from the Red Line Train, Foster Beach, Lake Shore Drive, Lake Front Trail, amazing Restaurants & a quality grocery store. You'll enjoy a clean & spacious 2 bedrooms apartment w/ friendly neighbors, flawless check-in & reserved parking. This place is safe & provides a beautiful & stocked apartment to relax after a busy day in the city. Short walk to Andersonville & Asia on Argyle for wonderful food options. The Riv &Aragon for concerts

A vibrant living area showcases eclectic décor, featuring a colorful mural with artistic motifs on one wall. A round coffee table sits in the center, surrounded by cream-colored sofas adorned with green cushions. A wet bar with wooden stools is visible in the background.

4.92 out of 5 average rating, 156 reviews

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.

Superhost

4.81 out of 5 average rating, 223 reviews

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!

4.99 out of 5 average rating, 300 reviews

A spacious living area features a red sofa, a coffee table, and a flat-screen TV mounted on a brick wall. Large windows allow natural light to fill the space. Decorative plants are positioned near the windows, accentuating the room's inviting atmosphere.

Condo in Chicago

Pets OK | Walk Score 95 | Desk | 1,750ft² |W/D

• 1,750ft² / 162m² . My home is on the first floor of a four flat Itallian Brick Building . You have 1 flight of stairs to climb to enter. • Walk Score 95 (walk to cafes, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Free street parking with pass included • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport Note: fireplace is not operational.

4.96 out of 5 average rating, 241 reviews

An open-concept loft showcases a cozy seating area with a grey couch adorned with yellow and patterned throw pillows. The kitchen, visible in the background, features modern appliances and a bar with two stools. A lofted sleeping area is bordered by a wooden railing.

Loft in Chicago

Lincoln Park Light-Filled Loft

Experience this unique Lincoln Park loft where you’ll love the open concept space, the floor to ceiling windows & the conveniences of your own two level suite. A converted store-front, this space is perfect for a couples weekend in Chicago, that friends get-away, or a place to call home for your small family vacation. Walk the neighborhoods & parks, and wonder why you’re not staying longer. We call this our little gem of a find, and are excited to share it with you. We love it, so will you!

4.99 out of 5 average rating, 101 reviews

A living area features natural light from multiple windows, complemented by a ceiling fan. A comfortable sofa with textured throws faces a modern fireplace. Two brown armchairs are positioned nearby, and a decorative rug lies under a coffee table, which displays a potted plant and a magazine.

Apartment in Evanston

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.

4.98 out of 5 average rating, 130 reviews

The living room is designed for comfort, featuring a spacious sectional sofa and a cozy armchair. A wooden coffee table sits on a striped area rug, while a TV is mounted on the wall. Decorative art and souvenirs are displayed, contributing to a travel-inspired vibe.

Guest suite in Chicago

Travelers Retreat in Old Town Chicago

Our garden unit is decorated with treasured souvenirs, maps, art, and decor that we’ve collected from all over the world to create a travel inspired retreat for Airbnb guests. Located in Old Town, a walkable neighborhood with famed architecture, stellar dining, stand-up/sketch comedy, and local shopping. Walking distance to Brown (Sedgwick) and Red (North/Clybourn) line trains. Centrally located between Downtown/River North and Lakeview/Wrigleyville. Adjacent to Gold Coast & Lincoln Park.

4.95 out of 5 average rating, 162 reviews

A modern chef's kitchen is shown, featuring an island with seating for four. Sleek dark cabinetry contrasts with light countertops and stainless steel appliances. A bowl of fruit adds a touch of color, while glass pendant lights provide illumination above the island.

Condo in Chicago

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

A row of historic brick homes is set along a tree-lined street. Each home features ornate details on the facade, with stairs leading to the entryways. Greenery and flowers enhance the surrounding gardens, adding to the neighborhood's vibrant character.

5 out of 5 average rating, 104 reviews

Lincoln Park DePaul Rowhouse Historic Bissell St

Exclusive Lincoln Park location. Beautiful historic landmarked block. Perfect for a weekend getaway or longer stay. You will have your own apartment with a private entry and brick patio to relax and enjoy coffee in this vibrant and historic neighborhood. Just a couple minute walk to exclusive Armitage Shopping District and DePaul University. Short walk to the lakefront, free Lincoln Park Zoo, Peggy Notebaert Nature Museum and Organic Farmer's Market during summer months.

A well-appointed bedroom features a spacious bed with layered linens and decorative pillows. Soft lighting from two bedside lamps complements a small desk and chair positioned near a window. Rich wood tones and a colorful area rug enhance the room's inviting atmosphere.

4.95 out of 5 average rating, 282 reviews

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 one flight of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

4.99 out of 5 average rating, 297 reviews

A light-filled living room showcases soft gray walls and hardwood flooring. A comfortable sofa and armchair are positioned around a decorative area rug. A television is mounted on a console, while a lamp beside a side table adds warmth to the space.

Condo in Chicago

Cozy 3BR on Chicago's North Side & Free Parking

Enjoy this charming 3-bedroom condo with free on-site parking just three blocks from Lake Michigan. Convenient access to public transit, including the express bus to downtown (9 miles), Navy Pier, and Grant Park. The CTA Jarvis station is only three blocks away. Perfect for families, business travelers, and couples, this condo is also close to Loyola (1.5 miles) and Northwestern universities (2.5 miles). A great home base to explore all that Chicago has to offer!

A cozy living room area features a dark leather sofa facing a mounted television on a wooden media console. A round shelf displays books and plants, while a small desk and chair are positioned beside a bright window.