
Vacation rentals with lake access in North Side
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Top-rated lake access rentals in North Side
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Soak Up Mid-Century Style in Wrigleyville and Boystown
This is an architecturally significant (3-bedroom 3.5-bathroom) home by noted Las Vegas architect Homer Rissman. We are located in the heart of East Lakeview, just half a block from Lake Michigan and Lincoln Park, and blocks away from Wrigley Field and Boystown. Smart TVs (with Netflix, Hulu, Amazon Prime) are located in the shared main level TV lounge, and also the lower level lounge. Entire home I like in-person check-in but full privacy is offered You will receive a link with detailed instructions within 24 hours of your check-in. If you have a U.S. mobile number, you will also receive a text message FULL DISCLOSURE: If you haven't used a lockbox (or don't know how to), self-check-in isn't for you. Your check-in should be in person. Lakeview is home to two of the most vibrant sports, nightlife, and theater scenes in Chicago: Wrigleyville and Boystown. Explore souvenir shops and casual eateries by day, and hop from bar to bar along Clark, Addison, and Sheffield Avenues by night. You walk to Treasure Island (half block), Jewel Osco (2 minutes), Whole Foods (4 minutes), Lakeview Athletic Club (4 minutes), XSports Fitness (5 minutes), Walgreens (3 blocks), bars and restaurants aound the corner. Close to multiple buses on Lake Shore Drive. Grab a bus to downtown in 15 minutes You will have to climb one flight of stairs for all bedrooms Street parking is free on the east side of Broadway. The west side requires 383 permits. Please, read the signs.
4.89 out of 5 average rating, 160 reviews
Chic Lincoln Park Townhome | Rooftop + Glam Bar
Welcome to The Lucky Penny! ⭐️ Lincoln Park Luxury | Rooftop + Glam Station | Sleeps 10 ⭐️ Stay in the heart of Lincoln Park, one of Chicago’s most vibrant neighborhoods, where tree-lined streets meet world-class dining, shopping, nightlife, and the lakefront. This beautifully curated 3-story townhome blends luxury, comfort & style, making it ideal for bachelorette weekends, girls’ trips, family stays, and celebratory group getaways. 📍 Steps from Lincoln Park Zoo, cafés, boutiques & lakefront
4.94 out of 5 average rating, 154 reviews
The Bright Retreat in Andersonville
Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark Street near some of Chicago's best restaurants. It is 3 blocks from the Argyle Red Line stop, which will get you to Wrigley in 15 minutes and downtown in 30 minutes. The home includes a fully stocked kitchen, free parking spot (small and medium size cars and SUVs only, not large vehicles), in unit washer & dryer, queen-size bed, and couch with queen-size memory foam mattress.
4.86 out of 5 average rating, 254 reviews
Archways at the Lincoln Park Zoo 2bed/2ba
Nestled in a historic 1920s renovated hotel, this apartment retains charming Art Deco arches that add a touch of history to its modern comforts. Featuring warm timber floors that connect two cozy bedrooms with queen beds to a contemporary kitchen. Each room has a TV, and the kitchen is fully stocked for your convenience. With two full bathrooms and barrier-free one-floor access, this space combines old-world charm with modern living in the vibrant heart of Lincoln Park, close to the Lakefront.
4.84 out of 5 average rating, 361 reviews
RockStar Pad W3A BoysTown/Wrigley Field/Parking
ROCKSTAR PAD @ W3A Chicago Wrigley Field/Boystown/Lakeview -Complete re-model, in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants & late night dining. -5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $20/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, robes, high speed WiFi, Sonos speakers, stylish design, washer & dryer & sugar free candy dish!
4.98 out of 5 average rating, 276 reviews
Modern Corner 2BR in Streeterville | Roof Deck | L
Stunning 1,200 square foot apartment with oversize windows, an open layout, and city/lake views in multiple directions. This bright and modern two bedroom, one bathroom corner unit is perfect for travelers looking for a stylish escape in the sky in downtown Chicago just off the Magnificent Mile and the lakefront. The building has great amenities including an amazing rooftop terrace with 360 degree views of the skyline and the lake. This is the best location in the city!
4.77 out of 5 average rating, 217 reviews
Your Chicago Retreat
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!
4.98 out of 5 average rating, 309 reviews
Guest Favorite Escape Next to the Beach
1st-floor unit with one flight of stairs. Older building with radiant heat managed by the building. Experience the best of Evanston in our cozy 1BR/1BA apartment near Lake Michigan. Enjoy a fully equipped kitchen, a comfortable bedroom with a queen bed, and a clean bathroom. Explore nearby beaches, stroll along the lakefront, and discover vibrant downtown shops and restaurants. Easy public transit to downtown Chicago. Book now for a memorable Evanston getaway!
4.9 out of 5 average rating, 149 reviews
Cozy loft in Chicago's Uptown
Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; apartment on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. Wrigley Field is a 5-minute drive. CTA's Red Line/Lawrence train station is only 1 block away. Parking decals available for guests (for parking overnight on surrounding residential streets).
4.97 out of 5 average rating, 343 reviews
Chicago Bootlegger House Sleeps 10-20
Walk to restaurants, groceries, shopping, Wrigley Field, Lake Michigan, Beaches, Boat Harbor, Lincoln Park Zoo, night life, bars, clubs, Red Line Train, Lakeshore Drive and more; all just a few blocks from your door. Giant house on 2 levels with over 3,500 square feet of living space and 6 bedrooms. Nicely decorated and lots of places to sit and mingle or watch one of the 85" TVs. Private 2 spot parking in garage and a parking pad for oversized vehicles.
4.96 out of 5 average rating, 165 reviews
Near Lake Michigan & Wrigley Field
Available 2B/2B condo with 2 King Size Beds. One block from the Aragon Ballroom and Riviera with great views of Uptown and two blocks from Lake Michigan. It’s also a perfect place to stay if your in town for a Cubs game. You can see the stadium from the rooftop deck. Walking distance to everything you need, 2 train stations, groceries, gym, restaurants/ bars. The perfect place to come and go as you please with easy key code entry.
4.98 out of 5 average rating, 366 reviews
Cozy Andersonville Cabin
Our cabin-in-the-city is a relaxing garden apartment, located in the popular LGBTQ+ friendly Andersonville area of Chicago. The cabin unit is decorated in bear and nature themes, with warm and cozy pine walls - like you were renting a cabin in the woods! Our place is a half a block from the main strip. Plenty of great shopping, award winning dining, and fun night life is just steps from our house!
4.98 out of 5 average rating, 175 reviewsPopular amenities for North Side lake access rentals
Lake access house rentals

Historic Old Town, Fabulous 4 Bedroom Home
4.87 out of 5 average rating, 212 reviews
Spacious Two Story Luxurious Home w/Outdoor Deck!
4.89 out of 5 average rating, 174 reviews
Superhost Wrigley/Lakeview Duplex 3BR/2.5BA
4.93 out of 5 average rating, 183 reviews
The Spa of Downtown Whiting
4.84 out of 5 average rating, 185 reviews
3 Luxury Master Suites by Gardens, Lake & Chicago
4.94 out of 5 average rating, 16 reviews
East Lakeview townhome near lake
4.86 out of 5 average rating, 28 reviews
Opulent 3bdr2bth Old Town Luxury + Parking prmts
4.97 out of 5 average rating, 96 reviews
*New* Luxury Wrigley Penthouse, Free Parking
4.94 out of 5 average rating, 62 reviewsLake access apartment rentals

5-Star Gold Coast Experience in a Luxe 2BR Retreat
4.94 out of 5 average rating, 142 reviews
Lakeview Charmer -with parking!
4.84 out of 5 average rating, 519 reviews
Evanston 2BR 2Bth 1 Blk to Beach
4.99 out of 5 average rating, 118 reviews
Midcentury Modern Lakeview 2 Bedroom Apartment
4.89 out of 5 average rating, 194 reviews
Charming, Sunny Apartment with Backyard Garden
4.97 out of 5 average rating, 550 reviews
Lux, spacious, bright, near Loyola-beach & subway
5.0 out of 5 average rating, 170 reviews
Luxury 3BR Duplex in Prime Location
4.99 out of 5 average rating, 113 reviews
Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
4.95 out of 5 average rating, 304 reviewsOther vacation rentals with lake access

2bd/2bath Urban Loft w/ 2 pkg spots 1 blk to train
4.88 out of 5 average rating, 893 reviews
Urban Comfort in the Heart of Chicago
4.99 out of 5 average rating, 719 reviews
A guest suite centrally located, but so quiet
4.97 out of 5 average rating, 299 reviews
Beautiful Lincoln Park/ De Paul Complimentary Parking Permit
4.98 out of 5 average rating, 339 reviews
Wrigleyville Condo 2 Blks from Lake & Train
4.87 out of 5 average rating, 154 reviews
Historic luxury townhouse on Chicago's Gold Coast
4.82 out of 5 average rating, 251 reviews
Spacious Rogers Park Apt Near Beach and CTA
4.82 out of 5 average rating, 77 reviews
Brand New Luxury space + roof deck!
4.94 out of 5 average rating, 70 reviewsDestinations to explore
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- Wrigley Field
- Soldier Field
- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
- Naval Station Great Lakes
- Indiana Dunes State Park
- 875 North Michigan Avenue
- Six Flags Great America
- University of Chicago
- The Field Museum
- Shedd Aquarium
- Humboldt Park
- Loyola University Chicago
- Guaranteed Rate Field
- Lincoln Park Zoo
- Union Park
- Frank Lloyd Wright Home and Studio
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- Donald E Stephens Convention Center
- Byline Bank Aragon Ballroom
- Washington Park Zoo
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