Waterfront vacation rentals in Near North Side, Chicago

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Near North Side, Chicago

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

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Guest favorite

Apartment in Chicago

4.91 out of 5 average rating, 183 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment 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 off the kitchen 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.

Apr 3 – 10

R7,491 ZAR per night

Guest favorite

Condo in Chicago

4.93 out of 5 average rating, 187 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or North Shore Evanston Hospital? This AirBnb is perfectly situated. An immaculately clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation - red line "El" trains & bus routes. Apt has a private, queen bedroom with en suite full bathroom, living room with queen sofa bed, TV, dining table and kitchenette. Dogs allowed and Parking available for a fee.

Dec 6 – 13

R1,810 ZAR per night

Superhost

Apartment in Chicago

4.86 out of 5 average rating, 153 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.

Sep 16 – 23

R7,312 ZAR per night

Superhost

Condo in Chicago

4.9 out of 5 average rating, 168 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!

May 7 – 14

R6,024 ZAR per night

Guest favorite

Apartment in Near West Side

4.97 out of 5 average rating, 66 reviews

Balcony EV charge w/ FREE Garage Parking Sleeps 8

FREE & SECURE ONE IN-DOOR PARKING SPOT!!! 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. Bring the whole family to this great place with lots of room for fun.

Jan 9 – 16

R3,169 ZAR per night

Guest favorite

Vacation home in Chicago

4.95 out of 5 average rating, 42 reviews

UChicago Luxurious King Suite Lakefront

Sink into a pillowtop king size bed in a sunny, spacious bedroom suite w/twin bed, his/hers closets and comfy love seat. Spacious 1,000 s.f. condo luxury, kitchens /bath with granite counters, office space, 3rd-floor unit, private entrance gated and on-street parking. Walk to beach, trails, golf course and bike rental. Located 1 blk from Express bus (15 minutes) to Univ of Chicago/Hyde Park and Museum of Science and Industry,(20 minutes) to Soldier Field, Grant Park, Downtown, Navy Pier

Dec 23 – 30

R2,347 ZAR per night

Superhost

Apartment in Edgewater

4.8 out of 5 average rating, 5 reviews

Lovely Lake Side Apartment

Enjoy a stylish experience at this centrally-located place. My studio apartment is right off of Lake Shore Drive. Across the street from Hollywood beach, a 4 minute walk. The 147 bus stop is right outside the apartment, which gets you downtown in 30 mins and the red line is a short 5-7 minute walk. The apartment is on the 12th floor with an amazing view of the city. The space is equipped with coffee station, records, books, art, and a great pantry of spices for those that enjoy cooking.

Sep 26 – Oct 3

R2,208 ZAR per night

Guest favorite

Guest suite in Evanston

4.97 out of 5 average rating, 214 reviews

A guest suite centrally located, but so quiet...

IF... you want to race into the city to see a play, go for a jog along the lake, have a quick coffee with a friend or enjoy a fine restaurant to celebrate a special occasion, it's all here in the lovely lakeside town of EVANSTON, IL. You can enjoy it all while living in my guest suite w/private kitchen, private bath, private entry, shared laundry area and......., if you need it, garage parking, too! Enjoy my garden on warm summer days; in winter, you will love the heated floor!

Feb 21 – 28

R2,816 ZAR per night

Superhost

Apartment in Chicago

4.79 out of 5 average rating, 140 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!

Oct 24 – 31

R9,284 ZAR per night

Guest favorite

Townhouse in Chicago

4.94 out of 5 average rating, 79 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.

Nov 28 – Dec 5

R9,637 ZAR per night

Guest favorite

Townhouse in Westmont

4.87 out of 5 average rating, 126 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.

Mar 8 – 15

R10,835 ZAR per night

Superhost

Home in Des Plaines

4.83 out of 5 average rating, 167 reviews

Exotic House - Few minutes from O'Hare and Chicago

Located in the heart of Des Plaines and close to Chicago, not only is the house comfortable but it is also convenient due to the accessibility to various locations including O’Hare International Airport, Downtown Chicago, I-90 and I-294 Expressways, Rivers Casino, Allstate Arena, Fashion Outlets of Chicago, a chain of restaurants within 2-mile radius, Des Plaines Metra Station, Lake Park and Lake Opeka, etc.

Jan 6 – 13

R4,132 ZAR per night