Waterfront holiday rentals in Chicago

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Chicago

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Superhost

Rental unit

4.83 out of 5 average rating, 177 reviews

The Lakefront Lookout (2BR)

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.

Guest favourite

Apartment

4.94 out of 5 average rating, 101 reviews

PING-PONG Free PARKiNG 10 min-Downtown Sleeps 10

ONE FREE INDOOR & SAFE PARKING SPOT INCLUDED! The building is next to a bus stop that brings you right into downtown! You would enjoy staying in the spacious 1800 sq ft with 10 ft high ceilings. 2 bedroom/2 bathroom apartment with ZERO STAIRS to get inside! It is an excellent solution for elder people and families with kids or maybe just a group of friends coming to have fun at the UNITED CENTER sports event or tourists as well as business folks or doctors to attend McCormick Place conferences.

Guest favourite

Rental unit

4.95 out of 5 average rating, 74 reviews

Loyola & Lake -3br/2bth close to the Lake & Loyola

Amazing lake views from 2 outdoor spaces! This spacious 3 bedroom, 2 bath unit has a large front balcony looking out to the lake and also a rear deck with lake views as well. The unit was recently renovated and has updated kitchen, bath & lots of entertaining space. In unit laundry and detergent included. Lots of books and games to keep you entertained! Walking distance to restaurants and bars. Starbucks is at the end of the block. Kayaks/paddle boards available for rent (May 1-Oct 15).

Guest favourite

Rental unit

4.92 out of 5 average rating, 214 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Guest favourite

Apartment

4.92 out of 5 average rating, 218 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed,TV, dining table, & partial kitchenette. Dogs only. Parking free on street or one spot for a fee.

Superhost

Apartment

4.88 out of 5 average rating, 179 reviews

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!

Guest favourite

Guest suite

4.94 out of 5 average rating, 288 reviews

Cozy Lakefront Retreat: Hot Tub & Bar/Pool Table

Very large guest suite with 3 separate areas. Just like your own apartment. Great for friends traveling together! ENTRANCE IS THRU THE MAIN PART OF THE HOUSE. This is just for the basement apartment but you have complete privacy down there. Fenced-in yard, hot tub, large patio, bbq, firepit, enjoy fishing or sitting watching the beautiful sunsets. Stocked lake, walking path, 3 parks! Check out the pictures to see all our home has to offer! (Full kitchen & laundry room are shared space)

Guest favourite

Rental unit

4.93 out of 5 average rating, 30 reviews

Sheridan Beach Apartment

Keep it central at this place! This basement apartment not only comes fully stocked with an in-unit washing machine, but a full kitchen with all new appliances. The unit is a PRIVATE apartment in a single-family home that is 10 steps away from the nearest CTA Bus stop, 2 blocks away from the redline, and ONLY 100 STEPS AWAY FROM THE BEACH on Lake Michigan 😄 Any and all drug use is a prohibited here. Any and all pets are prohibited here as this is a clean and newer construction.

Superhost

Rental unit

4.8 out of 5 average rating, 179 reviews

Spacious & Stylish 2BR-2BA Apt Steps from The Bean

Enjoy this comfy, renovated and super spacious 2BR and 2BA apartment in the heart of Chicago's Loop with views of Lake Michigan. Surrounded by the most popular stores and restaurants, this unbeatable location is less than a one-minute walk to Michigan Ave, Millennium Park, State St. Shopping, The Chicago Theatre and Chicago’s landmark, ‘The Bean'. It is an ideal location to move around in public transportation, as all CTA lines and plenty of bus lines are just within two blocks!

Guest favourite

Townhouse

4.94 out of 5 average rating, 111 reviews

Old Town/Lincoln Park Luxury Home Garage & Rooftop

Old town luxurious townhouse with rooftop, patio and attached garage (with Level 2 electric car charger for any type of electric car). The extra wide floor plan allows for 4 large bedrooms and 2.5 bathrooms spread over 4 levels of living. One block away from Brown Line station and 4 blocks away from Red Line station and best of Lincoln Park shopping. 10 minutes walk to North Avenue Beach or Lincoln Park Zoo. 5 minute walk to Second City, Zanies and Old Town dining & nightlife.

Guest favourite

Home

4.96 out of 5 average rating, 25 reviews

Lakefront Getaway Home! Lots of Fun! Amazing View!

INCREDIBLE 5,519 sq. LAKEFRONT HOME with GORGEOUS VIEWS. 30 Minutes Away From Downtown Chicago. 7 Bedrooms, 9 Beds, 2 Additional Sofa Beds & 4 Baths. Fits 20 guests by request. PRIVATE DOCK and PATIO/BACKYARD Right on BROOKERIDGE LAKE. UNICORN ISLAND FLOATING RAFT, KAYAK, PADDLE BOAT, FISHING & MORE. BrookeRidge Private Jet Airport in the Same Park. Indoor Entertainment Including POOL TABLE, AIR HOCKEY, PING PONG, DARTS, CARD GAMES, GAMING CONSOLE & KARAOKE 🎤

Guest favourite

Townhouse

4.87 out of 5 average rating, 128 reviews

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Near great shopping and dining. Enjoy wonderful sunsets and quiet lake activity. Fully Stocked 20 acres lake with a neighborhood beach next door. Easy commute to downtown while enjoying the peace and quiet. Feel like you are on vacation every day. Perfect for a staycation. Cleaned to Cdc standards. This duplex is a gem in Western suburbs! Pet friendly (fee). Fire pit (bring Wood), paddleboat, kayaks. Grill and fully stocked kitchen.