
Holiday rentals with lake access in Chicago
Find and book unique lake access rentals on Airbnb
Top-rated rentals with lake access in Chicago
Guests agree: these rentals with lake access are highly rated for location, cleanliness and more.

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.

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)
Welcome to this Old Town Masterpiece! Guests love this home because: - Steps away from top-notch restaurants/entertainment on bustling Wells St. - Close to every popular attraction that makes Chicago so great - Room for reg-size SUV in private driveway! - Luxurious interior design - Tranquil rooftop w/ grill - Fast WiFi - Pillow-top Bamboo mattress in each master en-suite - State of the art kitchen - Exceptional workspace - 5 minute walk from red line (CTA L) We look forward to hosting you!

Lincoln Pk-parking-wifi-King bd-crib-kid friendly
This wonderful 2 bedroom garden apartment in superhot Lincoln Park on a block where homes sell for 4 million to 12.5 million dollars. Walk score 97 The apartment was totally renovated adding new furniture, Flatscreen TVs in both bedrooms and Livingroom, a fully stocked kitchen, superfast wifi (150 Mbps) dedicated parking space, rooftop deck, washer, and dryer inside the apartment, see all that is offered below. The train (EL) stop is 2.5 blocks from the apartment. Go to the Cubs game/downtown.

Wrigleyville Condo 2 Blks from Lake & Train
I think you'll enjoy my spacious East Lakeview condo. The location is super convenient just 2 blks from Sheridan red line & 2 blks from the lake. Easy proximity 4 blks to Wrigley Field & restaurants/nightlife in Wrigleyville & Boystown. Amazing restaurant next door w/back patio- El Mariachi w/the freshest chips & guacamole! Starbucks, playground, and Divvy Bike station at the corner. 1 mi to Montrose Beach. All downtown sight-seeing easily accessible from Lake Shore Dr or red line 2 blks away.

Corner 3BR in Streeterville | Views | Roof Deck
Stunning 1,500+ square foot corner apartment with oversize windows, an open layout, and dramatic city and lake views in multiple directions. This bright and modern three bedroom, two bathroom apartment 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!

RockStar Pad W3A BoysTown/Wrigley Field/Parking lot
HAVE IT ALL @ W3A Chicago Wrigley Field/Boystown/Lakeview -Newly renovated like new in safe centrally located East Lakeview. -10 min walk to Wrigley Field, Boys town, beaches, super markets, restaurants with late night dining. 5 min walk to Metro Sheridan Red Line (direct downtown), private enclosed parking $10/night & or free permits for street parking -600 thread count linens, fluffy soft pillows, house coats, high speed WiFi, Sonos speakers, stylish design & in unit washer & dryer

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.

GLORIOUS GOLD COAST GETAWAY
Welcome! Amazing Gold Coast/Streeterville location SECONDS from the LAKE and MAGNIFICENT MILE. Located on a quiet street, this apartment is tucked in between Michigan Ave and Lake Michigan. Steps away from the famous Drake Hotel, yet closer to the lake and Oak Street Beach. This spot is considered the best location in the city-- steps away from the best stores/restaurants in the world located on Michigan Ave (Mag Mile) and just north of Navy Pier. We look forward to hosting you!

Steps to Mag Mile, 2 BD , fast Wi-Fi, W&D
Private 2BR apt. in vintage 3-flat in the heart of Chicago's Michigan Ave/Gold Coast neighborhood. Fantastic locations steps from world-class shopping and restaurants, Oak St. beach, and public transportation (L trains, express bus). Includes A/C, washer-dryer, super-fast wi-fi, smart TV, and workspace. Hourly rate garage parking next door. Note: Guests must walk up one flight of stairs. Light sleepers should bring earplugs as there are noises typical of a big city.

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.

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. Itโs 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.

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit
This generously sized, quiet apartment, located in the highly sought-after Lincoln Park neighborhood, offers convenient access to acclaimed restaurants and boutiques, all within a five-minute walk. Its private entrance and proximityโless than four blocksโto both the Red and Brown Line "L" stations ensure effortless access to Chicago's attractions, most within a two- to five-stop train ride. Zoned parking permits are provided.
Popular amenities for lake access rentals in Chicago
Lake access house rentals

Spacious Two Story Luxurious Home w/Outdoor Deck!

Amazing historic campus mansion!

CasaNova Modern City Living

Lakefront View Getaway Home! Hot tub! Kayak!

Two Kings Chicago. Royal comfort in two king beds

Sleepy sanctuary

Private Downtown Retreat with Rooftop Oasis

Opulent 3bdr2bth Old Town Luxury + Parking prmts
Apartment rentals with lake access

Evanston 2BR 2Bth 1 Blk to Beach

Spacious Vintage 3 BR in Chicago's NorthCenter!

Charming, Sunny Apartment with Backyard Garden

Upscale High-Rise Apt ยท Rooftop Pool + Views

The Posh Apt. Mins to Downtown & Hyde Park

New renovation|1BR|Stylish|Modern|Next to the Lake

Charming Apt.Fully Equipped Prk.Inc 12 min 2 Lake

COZY unit near Michigan Lake 2nd floor/no elevator
Other holiday rentals with lake access

Pristine Lakeview l Boystown l Wrigley HavenlBeach

13 mins DT | 4 mins Lake | Regal Style Loft Rooftop

The Landing @ South Loop

The Wine Down

Spacious 3BR in Lakeview - Walk to Wrigley & Shops

cozy grand studio 2nd floor/near lake/public tran.

Jarvis Gardens - 1BR/BEACH/Wine patio/fire pit

UChicago Luxurious King Suite Lakefront
When is the best time to visit Chicago?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $169 SGD | $164 SGD | $191 SGD | $197 SGD | $237 SGD | $253 SGD | $266 SGD | $261 SGD | $242 SGD | $241 SGD | $214 SGD | $197 SGD |
| Avg. temp | -3ยฐC | -1ยฐC | 4ยฐC | 10ยฐC | 16ยฐC | 22ยฐC | 25ยฐC | 24ยฐC | 20ยฐC | 13ยฐC | 6ยฐC | 0ยฐC |
Quick stats about holiday rentals with lake access in Chicago

Total holiday rentals
Explore 580 holiday rentals in Chicago

Nightly prices starting at
Chicago holiday rentals start at $25ย SGD per night before taxes and fees

Verified guest reviews
Over 35,580 verified reviews to help you choose

Family-friendly holiday rentals
320 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 200 rentals that welcome pets

Holiday rentals with a pool
100 properties feature pools

Rentals with dedicated workspaces
460 properties have a dedicated workspace

Wifi availability
570 of Chicago holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chicago rentals

4.8 Average rating
Chicago stays are highly rated by guests โ averaging 4.8 out of 5!

Nearby attractions
Chicagoโs top spots include Millennium Park, Wrigley Field and Lincoln Park
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- Millennium Park
- Wrigley Field
- United Center
- Grant Park
- Navy Pier
- Chicago River Walk
- Soldier Field
- 875 North Michigan Avenue
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- Humboldt Park
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- Guaranteed Rate Field
- The Field Museum
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- Frank Lloyd Wright Home and Studio
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- Washington Park Zoo
- University of Chicago
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