Waterfront vacation rentals in Chicago Loop

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Chicago Loop

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

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Superhost

A rooftop terrace features various seating options, including lounge chairs and circular lounges. Colorful cushions are arranged on some seats, while green planters add a touch of nature. The skyline of Chicago is visible in the background under a clear blue sky.

Apartment in Gold Coast

4.82 out of 5 average rating, 191 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 favorite

The historic stone façade of the building features intricate architectural details, with large arched windows and a welcoming entrance. Flower pots are displayed on the balcony, and a wrought iron fence surrounds the property, adding to the charm of the exterior.

Apartment in Lake View

4.92 out of 5 average rating, 226 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.

Superhost

A spacious living area features a large sectional sofa facing a media unit with a TV, accompanied by a coffee table. A dining table with four chairs sits nearby. Floor-to-ceiling windows provide bright natural light and a view of adjacent buildings.

Condo in Gold Coast

4.88 out of 5 average rating, 192 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!

Top guest favorite

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 Gold Coast

4.95 out of 5 average rating, 116 reviews

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

Superhost

The studio apartment features a spacious open layout with a comfortable bed, muted bedding, and a nightstand. A TV is positioned on a modern media unit, and a mini fridge adds convenience. Natural light filters in through a window, illuminating the neutral decor.

Condo in Magnificent Mile

4.7 out of 5 average rating, 223 reviews

Studio flat in the heart of Chicago's Gold Coast

Fully equipped 1 bedroom studio apartment in the heart of Chicago's Gold Coast. Situated on the lower floor, our basement suite apartment has all you will need to call it 'home' for your stay. With the comfiest bed, highest quality linen and luxury bathroom, it is perfect for chilled evenings in after exploring many of Chicago's amazing locations all within walking distance. We are located in the middle of Downtown Chicago, a short walk to the Original Pancake House, Gibsons and the beach!

Superhost

The living area features a light-colored sofa paired with two cozy armchairs. A round coffee table sits at the center on a colorful area rug. Natural light floods the space through two large windows, and decorative plants are placed on the windowsills.

Apartment in The Loop

4.81 out of 5 average rating, 195 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 favorite

A spacious bedroom features a king-size bed dressed in white linens, accented by a mustard yellow throw. Nightstands with lamps are positioned on either side of the bed. A decorative rug adds softness to the warm-toned wood flooring, with natural light streaming from the patio doors.

Townhouse in Old Town

4.94 out of 5 average rating, 125 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 favorite

A modern living room features a light gray sofa paired with dark accent pillows. Natural light fills the space through large windows, complemented by dark curtains. A stylish armchair and a side table sit next to the sofa, while a flat-screen TV is mounted on the wall.

Apartment in Near West Side

4.97 out of 5 average rating, 115 reviews

Free Parking| King Bed |Private Balcony |Sleeps 8

Your stylish city escape—unwind, explore, and experience Chicago like never before. Our modern, spacious condo is perfect for families, groups, and business travelers looking for a comfortable, stylish, and well-located stay. Whether you're in town for a concert, conference, sightseeing, or a weekend getaway, you'll find everything you need for a relaxing stay. ONE SECURE INDOOR PARKING SPOT IS INCLUDED❗❗❗ ✨ Book your stay today & experience Chicago in comfort and style! ✨

Top guest favorite

A spacious bedroom features a large bed with soft bedding and multiple pillows. Dark walls create a cozy ambiance, complemented by stylish artwork. A glass table and chairs are visible, along with a modern ceiling fan and a bright window providing natural light.

Apartment in East Rogers Park

4.95 out of 5 average rating, 80 reviews

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

Amazing lake views from 2 outdoor spaces! This lovely 3 bedroom, 2 bath unit has a large front balcony and also a rear deck looking out to the lake. The unit has an updated kitchen & 2 baths, a dining area, in unit laundry & a spacious living room with a fireplace & lots of books and games to keep you entertained! Walking distance to restaurants and bars. Starbucks is a short walk down Sheridan. Kayak/paddle board rental available (May 1-Oct 15th), weather permitting.

Guest favorite

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

Condo in East Rogers Park

4.92 out of 5 average rating, 230 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy 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. Note: no full kitchen.

Guest favorite

Townhouse in Westmont

4.87 out of 5 average rating, 130 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.

Superhost

A welcoming living space features a round dining table surrounded by four chairs, with a large artwork depicting trees on the wall. A light fixture hangs from the ceiling, and a mirror reflects the room. Natural light fills the area, enhancing the warm ambiance.

Apartment in Evanston

4.83 out of 5 average rating, 178 reviews

MDRN Kid-Frndly Apt | Natural Lite | Quiet|Private

Relax with the whole family or explore the city with friends at this peaceful and spacious 3-bd/1.5 ba condo tucked on a quiet, tree-lined street. Includes one (1) free parking space, plus plenty of unmetered parking on st. Minutes away notable hospitals, both Northwestern, and Loyola Universities. Travel via CTA bus stop at the corner. Only 30min drive from downtown Chicago. PET & 420 FRIENDLY!

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What guests are saying

Tranquility Awaits You!

5 out of 5 average rating, 7 reviews8 months ago

Mrs Jackie was a wonderful person to meet she was like another mother to me. She was very helpful and made you feel right at home. She gave her residents privacy you wouldn’t even know she was there but was there if we had any concerns or questions taught us some history about her home and herself the stay was so quiet and peaceful I didn’t want to leave! The parking was great the area was beautiful and it was about 45 minutes from the city which was still a wonderful drive to site see. Mrs. Jackie made me feel welcome coming and when it was time to go. If you were religious she had a place you can read the word or pray even if you wanted to go outside on the deck just beautiful. Kitchen was open if you wanted to cook instead of eating out as long as you cleaned up after yourself theater was amazing felt like you were really at the movies. Jacuzzi was nice at night and peaceful. I highly recommend your stay here she was an awesome and amazing host. When I come back this is the spot!

Private room in Burr Ridge

What guests are saying

Basic accomodation equipped for short terms stays.

4.76 out of 5 average rating, 167 reviews4 weeks ago

This was my second stay at Emy's. I really enjoyed all the cafes and shops nearby. It is a great location with access to both trains and buses, that go to the loop. You can also, get to Wicker park easily as well as the many music venues around the city. I would recommend Emy's to anyone wanting to visit Chicago, I had a great stay.

Private room in Lincoln Square

What guests are saying

Historic Manor House Private Room #1 in Evanston

5 out of 5 average rating, 14 reviews7 months ago

I can’t praise this place enough. Not only was it more beautiful than the pictures, but Janet also provided amenities above and beyond what was listed. She provided towels, sunscreen, and a beach pass and the house is in walking distance to Lake Michigan. She was always quickly able to answer any questions and was readily available. Janet really tries to make the space feel at home and provides you with everything you need for a comfortable stay. I was surprised by the quality and ease of the entire stay, and the room was gorgeous (lots of natural light and plenty of privacy). I HIGHLY recommend this location for an Evanston visit (walking distance to downtown and the lake) as well as the excellent service I received from Janet.

Private room in Evanston

What guests are saying

HUGE & BRAND NEW BEACH Apartment is Ready For You!

4.52 out of 5 average rating, 48 reviews7 months ago

Liz’s Airbnb was a perfect base of operations for me and my husband. The space was roomy and comfortable. We were gone lots for events around a family member’s birthday, but also enjoyed our time at and around the Airbnb. We especially enjoyed Loyola Beach, a short walk from Liz’s place. Lake Michigan water temps were lovely.

Apartment in East Rogers Park

What guests are saying

Ideal Evanston downtown apartment with porch, view

4.89 out of 5 average rating, 218 reviews2 days ago

This place located in the center of Evanston very close to both downtown Evanston and the Northwestern University. Kerry is a very caring and responsive host. She’s also very elegant and so is her apartment. I had a wonderful stay there and hope to come back again.

Private room in Evanston

What guests are saying

Beautiful Studio just across from the beach!

4.34 out of 5 average rating, 32 reviews7 months ago

The property was as described and Christina was an exceptional host. She checked in with us to make sure we were okay and asked if we needed anything a couple of times during our stay and was very attentive. The property was quiet, private, and what we needed for our short stay. Check-in was very easy. We appreciate the attentiveness.

Apartment in Edgewater

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