
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.
NearbyOutdoor spacesCheck-in
4.89 out of 5 average rating, 160 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.
Outdoor spacesNearbyParking
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.
NearbyViewFamily
4.84 out of 5 average rating, 361 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.
NearbyViewAir conditioning
4.92 out of 5 average rating, 290 reviews
RockStar Pad W3A Chicago-Wrigley/BoysTown/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!
NearbyViewLong stay
4.98 out of 5 average rating, 277 reviews
Lakeview Charmer -with parking!
Walk to Wrigley 4 blocks away: 15 min walk; 3 minute drive. Walk to The Vic (around the corner), the lake, several theaters, many restaurants, RedLine el (1 block) takes you north to Evanston, south to Loop, to Sox. Park your car behind the building. A Garden 2 BR (one semi-private; see pics) with 2 queen beds. With rollaway and couch, could accommodate up to 6. We also have a fold up crib. FYI: NO Smoking inside or on the patio. No animals. See pic on patio: el is a few doors west.
NearbyViewComfort
4.84 out of 5 average rating, 520 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 private guest suite w/kitchenette, 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!
Outdoor spacesNearbyComfort
4.97 out of 5 average rating, 301 reviews
Historic Old Town, Fabulous 4 Bedroom Home
Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck! License Pending.
NearbyOutdoor spacesLaundry
4.87 out of 5 average rating, 212 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).
NearbyLocationBeach
4.97 out of 5 average rating, 343 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.
NearbyViewLong stay
4.98 out of 5 average rating, 368 reviews
Executive Apartment on Lake Michigan with parking
Stay in a furnished 2nd-floor apartment in a walk-in building with its own beach on Lake Michigan. Watch the waves from your living room or sit out on the terrace. -Free Wifi, -Onsite Parking with EV charging station -Steps away from parks, minutes away from universities, shopping, and restaurants -Less than 25 min drive to Wrigley Field, Downtown Chicago, Soldier Field, and museums.
ViewNearbyCheck-in
4.9 out of 5 average rating, 225 reviews
Urban Comfort in the Heart of Chicago
This is the PRIVATE first floor of our duplex condo, with your own entrance/exit, 75" flatscreen TV, central heat/air, and an en-suite bathroom. We are in the middle of Chicago's vibrant Northside while still having the benefit of coming home to a tree lined one lane residential street. Please contact us with any questions at all before you book your stay.
ViewNearbyHeating
4.99 out of 5 average rating, 719 reviewsPopular amenities for North Side lake access rentals
Lake access house rentals

Spacious Two Story Luxurious Home w/Outdoor Deck!
NearbyOutdoor spacesWalkability
4.89 out of 5 average rating, 175 reviews
Superhost Wrigley/Lakeview Duplex 3BR/2.5BA
NearbyGetting aroundBiking
4.93 out of 5 average rating, 184 reviews
Modern Farmhouse In Andersonville- No cleaning fee
NearbyAmenitiesCleanliness
4.94 out of 5 average rating, 98 reviews
Huge Downtown Gem *Yard *Parking *Fireplace
NearbyOutdoor spacesCleanliness
4.89 out of 5 average rating, 166 reviews
The Spa of Downtown Whiting
NearbyViewHeating
4.84 out of 5 average rating, 185 reviews
3 Luxury Master Suites by Gardens, Lake & Chicago
NearbyOutdoor spacesBathroom
4.94 out of 5 average rating, 16 reviews
Opulent 3bdr2bth Old Town Luxury + Parking prmts
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4.97 out of 5 average rating, 96 reviews
East Lakeview townhome near lake
NearbyOutdoor spacesFamily
4.86 out of 5 average rating, 29 reviewsLake access apartment rentals

Evanston 2BR 2Bth 1 Blk to Beach
Outdoor spacesViewAccess
4.99 out of 5 average rating, 118 reviews
Penthouse Corner 2BR in Streeterville | Roof Deck
NearbyViewValue
4.78 out of 5 average rating, 240 reviews
OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)
Outdoor spacesNearbyIndoor spaces
4.94 out of 5 average rating, 260 reviews
Charming, Sunny Apartment with Backyard Garden
Outdoor spacesNearbyLocation
4.97 out of 5 average rating, 551 reviews
Midcentury Modern Lakeview 2 Bedroom Apartment
ViewOutdoor spacesDecor
4.89 out of 5 average rating, 194 reviews
Guest Favorite Escape Next to the Beach
ViewOutdoor spacesSolo travel
4.9 out of 5 average rating, 149 reviews
Luxury 3BR Duplex in Prime Location
NearbyOutdoor spacesHospitality
4.99 out of 5 average rating, 113 reviews
Lux, spacious, bright, near Loyola-beach & subway
Outdoor spacesNearbyHospitality
5.0 out of 5 average rating, 171 reviewsOther vacation rentals with lake access

Your Chicago Retreat
Outdoor spacesNearbyAmenities
4.98 out of 5 average rating, 309 reviews
Cozy Andersonville Cabin
NearbyCheckoutLocation
4.98 out of 5 average rating, 175 reviews
Beautiful Lincoln Park/ De Paul Complimentary Parking Permit
ViewOutdoor spacesSleep quality
4.98 out of 5 average rating, 339 reviews
Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit
Outdoor spacesViewAir conditioning
4.98 out of 5 average rating, 99 reviews
Spacious Rogers Park Apt Near Beach and CTA
ViewNearbyBeach
4.82 out of 5 average rating, 78 reviews
Brand New Luxury space + roof deck!
ViewNearbyGetting around
4.94 out of 5 average rating, 70 reviews
Spacious Wrigleyville 1-Bedroom
Indoor spacesQuietCondition
5.0 out of 5 average rating, 4 reviews
The Holiday House by the Lake! 2br/2bth
Outdoor spacesViewAmenities
4.96 out of 5 average rating, 92 reviewsDestinations to explore
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- Wrigley Field
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- Lincoln Park
- United Center
- Grant Park
- Navy Pier
- Millennium Park
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- 875 North Michigan Avenue
- University of Chicago
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