
Vacation rentals with lake access in Woodlawn
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Top-rated lake access rentals in Woodlawn
Guests agree: these lake access rentals are highly rated for location, cleanliness, and more.

Stunning 3BR Penthouse in the Loop | Roof Deck
[NOTE: The main rooftop is currently closed for renovations and is slated to reopen in Summer/Fall 2026. The 2nd rooftop remains open and available to use, including the pool which typically opens around Memorial Day]. Beautiful 1,400+ square foot penthouse apartment on the top floor with 13 foot tall ceilings, oversize windows, and panoramic city views. This bright and airy three bedroom, two bathroom space is perfect for travelers looking for a luxurious escape in the sky in the heart of down

The Spa of Downtown Whiting
so close to Chicago but so far away. NEWLY REMODELED AND COMPLETELY FURNISHED. There's so much to enjoy in this incredible converted 2 flat, now a single unit. WE COMPLETELY RIPPED ON AND REDID THE ENTIRE INTERIOR. 1ST Flr-spa w/ 2 person jacuzzi, shower, continuous hot water, family room, kitchen 2nd flr, sitting room w/ TV and surround sound, 2 bedrooms, w/ bathroom and bath/shower. -FRONT BALCONY, -SPEAKERS THROUGHOUT -BLOCKS FROM THE BEACH & WOLFE LAKE -PERFECT LOCATION FOR PIEROGIFEST

Cozy 2 bdrm near McCormick Place & Wintrust Arena
Come enjoy Chicago via our cozy apartment in the quiet yet friendly Historical Bronzeville community. We are nestled between Hyde Park and South Loop, where you will find plenty of restaurants, theaters, and nightlife. Only minutes away from McCormick Place, 10-15 min drive from downtown and 3-12 miles from all the sports arenas and airports. You can bike or walk to the nearest grocery store, park, gym, and beach. The nearest bus and/or train is 2-3 blocks away for your convenience as well.

Evanston 2BR 2Bth 1 Blk to Beach
With its older charm, modern comforts, and unbeatable proximity to the beach, this 2-bedroom, 2-bath unit offers an ideal getaway. Only 1 block from beautiful Lake Michigan and South Blvd Beach, you will love our spacious, sunny apt. Whether you're staying for a short visit or a lengthy one, you'll feel the comfort of home on a tree-lined street. The unit has hardwood floors throughout, comfortable bedrooms, a fully stocked kitchen, dining room, and a sunroom looking out on the backyard patio.

420 at Cheltenham 4BR
If you want to experience an authentic piece of Chicago and it’s rich history, our place is a cozy spot to start and it’s just like being at home. Summertime Chicago Lake Shore Drive Beaches. Lollapalooza. Chicago Riverwalk. Concerts at Soldiers Field-Bears. Winter wonder festival. The Bean. Great for larger groups visiting looking to divide costs. Obama Library, Southshore golf course, Reggies on the Beach, Shedd Aquarium, Field Museum, Museum of Science & Industry are all within 20 minutes.

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.

Spacious 4-Level/4-Bedroom Townhouse in West Loop
Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

Chic Lincoln Park Townhome | Rooftop + Glam Bar
⭐️ 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, and style, making it ideal for bachelorette weekends, girls’ trips, family stays, and celebratory group getaways. 📍 Steps from Lincoln Park Zoo, cafés, boutiques & the lakefront

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!

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!

MICH AVE Downtown, Park, Museums 2bd #4
Feel at Home, Unwind, and Enjoy the amenities you deserve next to Grant Park! Most homes don’t provide professional service along with “local vibes.” Guests love staying with us because: ✅ Central location close to Museum Campus ✅ Parking Garage attached to the building ($15-30 / night) ✅ FAST WIFI ✅ Big, Comfy KING beds ✅ Rooftop Deck ✅ 1 block from the Red, Orange, Green L subway stops ✅ Close proximity to Grant Park, Soldier Field, Museums & more!

Secluded 2BR APT in Chinatown by McCormick/DWTN
Located in the heart of Chinatown and close to McCormick Place, with easy access to public transportation into the city. Chinatown is the largest Asian neighborhood in the city with food choices such as Chinese Cuisine, Dim Sum, Asian Fusion, and Szechwan cooking . You don't want to miss the bubble tea, Thai ice cream, and crepes. Please note that our photos are not professionally captured in order to show the true view of our unit.
Popular amenities for Woodlawn lake access rentals
Lake access house rentals

Uptown Townhouse - Walk to Lake Front and Red Line

B42: Spacious w/ Modern Art/Decor Mins to DWTN

CasaNova Modern City Living

Historic Old Town, Fabulous 4 Bedroom Home

Three Kings Chicago. Royal experience. Cloud beds!

Luxury 3 BR Greystone Near Obama Center

Private Downtown Retreat with Rooftop Oasis

*New* Luxury Wrigley Penthouse, Free Parking
Lake access apartment rentals

Upscale High-Rise Apt · Rooftop Pool + Views

The Lakefront Lookout (Rooftop Deck • Gym)

Bronzeville Bohemian Loft

Lincoln Pk-parking-wifi-King bd-crib-kid friendly

OLD TOWN TRIUMPHANT 2BD/2BA (+Rooftop&Parking)

Andersonville Living

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

Midcentury Modern Lakeview 2 Bedroom Apartment
Other vacation rentals with lake access

Hyde park! 2min UofC 6mi downtown!

Archways at the Lincoln Park Zoo 2bed/2ba

Home in Chicago Woodlawn. Walk to Obama Library!

Elegant Rogers Park Home for 8 guest w/parking

Woodlawn Oasis | Modern 3BR Near UChicago

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

Condo in Chicago Bronzeville 9 mins to Downtown #3

Stylish Hyde Park/Kenwood Brownstone Garden Apt
When is the best time to visit Woodlawn?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ 261 | ﺩ.ﺇ 279 | ﺩ.ﺇ 334 | ﺩ.ﺇ 261 | ﺩ.ﺇ 437 | ﺩ.ﺇ 441 | ﺩ.ﺇ 371 | ﺩ.ﺇ 279 | ﺩ.ﺇ 202 | ﺩ.ﺇ 264 | ﺩ.ﺇ 198 | ﺩ.ﺇ 228 |
| Avg. temp | -3°C | -1°C | 4°C | 10°C | 16°C | 22°C | 25°C | 24°C | 20°C | 13°C | 6°C | 0°C |
Quick stats about vacation rentals with lake access in Woodlawn

Total vacation rentals
Explore 30 vacation rentals in Woodlawn

Nightly prices starting at
Woodlawn vacation rentals start at ﺩ.ﺇ 110 per night before taxes and fees

Verified guest reviews
Over 860 verified reviews to help you choose

Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
30 of Woodlawn vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Woodlawn rentals
Destinations to explore
- Rentals with a washer and dryer Woodlawn
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- Rentals with outdoor seating Woodlawn
- Rentals with beach access Woodlawn
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- Rentals with lake access Chicago
- Rentals with lake access Cook County
- Rentals with lake access Illinois
- Rentals with lake access United States
- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Grant Park
- Navy Pier
- Soldier Field
- 875 North Michigan Avenue
- The Field Museum
- Six Flags Great America
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Union Park
- University of Chicago
- Lincoln Park Zoo
- Chicago River Walk
- Frank Lloyd Wright Home and Studio
- Garfield Park Conservatory
- Washington Park Zoo
- Loyola University Chicago
- Indiana Dunes State Park
- Oak Street Beach
- Illinois Beach State Park





