
Condo vacation rentals in Near North Side
Find and book unique condos on Airbnb
Top-rated condo rentals in Near North Side
Guests agree: these condos are highly rated for location, cleanliness, and more.

Modern MAG Mile 2BD/2BA (+Parking/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 - Parking spot on-site in/out access!! - Tranquil rooftop overlooks Lake - Fast WIFI - Super comfy beds! - Custom chef kitchen - Located on a quiet street - Lake Michigan view from our floor-to-ceiling windows

❤︎ of Lincoln Park | 11ft Ceiling | 1,750ft² | W/D
• 1,750ft² / 162m² . My home is on the second floor of a four flat Itallian Brick Building . You have 2 flight of stairs to Climb to enter. • Walk Score 95 (walk to cafe's, bars, eating, nightlife, etc.) • Biker's paradise • Fully equipped + stocked kitchen • Extremely safe neighborhood • Onsite, secured parking • Onsite washer + dryer ➠ 5 min walk to the Lincoln Park ➠ 10 min drive to Downtown Chicago ➠ 30 min drive to O'Hare Chicago Airport fireplace is not operational.

Private hot tub - King bed suite - Free parking
Welcome to this urban retreat in the heart of Chicago's Little Italy neighborhood. Conveniently located adjacent to Chicago's downtown Loop and West Loop neighborhoods, you will find endless opportunities to experience the best of Chicago. At the end of your day, enjoy a relaxing soak in your private outdoor hot tub (open year-round) before sinking in to your Tempur-Pedic king bed for a restful night's sleep. Complimentary off-street parking provides rare convenience near the city center.

Downtown Chicago - Spa Bath, Patio, 3 blocks to L
Explore Chicago's charm just moments from downtown! This Airbnb boasts a spa bath with a luxurious rain shower and jetted tub, a fully equipped kitchen for culinary adventures, comfortable reclining sofas for relaxation, and ample space to unwind. Sleep like royalty in the master bedroom's king bed, and a queen murphy bed in the living area ensures a comfortable stay for up to four guests. Step outside to the patio with a fire pit for cozy evenings. Your Windy City getaway begins here!

Brilliant Downtown Chicago 3-Bedroom Condominium
Situated in downtown Chicago, right next to the Godfrey Hotel, this spacious and bright 3-bedroom, 2-bathroom condominium is perfectly suited to deliver the best adventures the Windy City has to offer. Our vacation home includes four sleeping areas with 1 King & 3 Queen sized memory foam mattresses and features everything from a fully-stocked kitchen to smart gadgets like Alexa. PARKING: We offer a $30 per day parking credit. This credit pays for most or all parking costs.

MARVELOUS MAG MILE 2BD/2BA (+Rooftop)
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.

Modern Izakaya Studio in Wicker Park
Stay in a sleek underground izakaya themed studio in one of Chicago's most desirable neighborhoods. Relax and enjoy the quiet zen decor. Find our hidden Japanese whisky room. Kick back in our pillowy loungers and dig into our ramen selection... The Izakaya Studio in the heart of Wicker Park is about giving you a uniquely luxurious guest experience from which to begin your adventures in Chicago.

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 a newly remodeled 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.

Great location. Free parking.
Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

Old Town Modern | Elevator, Parking, Terrace
Welcome to Old Town Modern! Thoughtfully designed 2 bedroom/2 bath light filled condo with 13ft ceilings, private terrace and underground parking in a secure, elevator building. You'll be in the heart of the Old Town on Wells St with world-class dining right outside the door, short walk to Second City, Lincoln Park Zoo, and North Avenue Beach.

River North Hideaway w/Amazing Views and Parking
In the heart of River North, this stylish retreat offers amazing city views, an ensuite bathroom for added comfort, and the convenience of an in-unit washer and dryer. Enjoy secure garage parking and a vibrant neighborhood full of top dining, nightlife, and shopping just steps away. Registration Number: R25000125394

Unique Lincoln Park Duplex Apt
Unique apartment duplex in the heart of Lincoln Park on a quiet residential street; jus a few blocks away from Lincoln Park Zoo and DePaul University, walking distance to the lakefront and easily accessible public transportation.
Popular amenities for Near North Side condo rentals
Weekly condo rentals

Studio flat in the heart of Chicago's Gold Coast

Lincoln Square Gem!

Newly updated 1BD/1B in Old Irving Chicago!

Near McCormick Place and Minutes from Downtown!

Near Lake Michigan & Wrigley Field

Spacious 4 Bedroom Condo

Modern Luxury In Old Town - Sleeps 4

Large 2BR, 2BA, patio, sunroom, W/D, L-kitchen
Pet-friendly condo rentals

Chic and Charming Vintage Condominium in Lincoln Park

Cozy Lincoln Park Condo near the lake.

Spacious 3BR • Great for Groups • Fast WiFi • Pets

Wrigley Residence in Iconic Wrigley Rooftop

Spacious 3BR/3BA Condo in Trendy Ukrainian Village

Luxuriously bright 3-bedroom condo: The Treehouse

Picture Perfect 3Bed Steps from Train and FLW

Can't Beat This 2min Walk to Wrigley!
Condo rentals with a pool

"Joy of Evanston" 1BDR, KING EXEC Suite, pool+Gym

"Bliss of Evanston" 180°view, 2BDR +2Bath Urbanlux

Harmony of Evanston 1 BDR Exec Suite w/pool & Gym

Best view and luxury style, Located in Downtown

Lovely 2 Bed 2 Bathroom!

Chicago's Treasure "Heart of Evanston" 2bdr +1 Ba

"Unity of Evanston" 3 BDR+2BA ModernLuxe +pool

Iconic Style, Charming Lake View
When is the best time to visit Near North Side?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $183 CAD | $182 CAD | $193 CAD | $228 CAD | $238 CAD | $245 CAD | $245 CAD | $245 CAD | $201 CAD | $210 CAD | $194 CAD | $201 CAD |
| 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 condo rentals in Near North Side

Total vacation rentals
Explore 130 vacation rentals in Near North Side

Nightly prices starting at
Near North Side vacation rentals start at $28 CAD per night before taxes and fees

Verified guest reviews
Over 5,260 verified reviews to help you choose

Family-friendly vacation rentals
60 properties offer extra space and kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Vacation rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
80 properties have a dedicated workspace

Wifi availability
130 of Near North Side vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Near North Side rentals

4.8 Average rating
Near North Side stays are highly rated by guests—averaging 4.8 out of 5!

Nearby attractions
Near North Side’s top spots, include 875 North Michigan Avenue, Chicago Riverwalk, and Museum of Contemporary Art Chicago
Destinations to explore
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- Rentals with pools Near North Side
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- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- 875 North Michigan Avenue
- Humboldt Park
- Shedd Aquarium
- Guaranteed Rate Field
- Oak Street Beach
- The Field Museum
- Garfield Park Conservatory
- Wicker Park
- Lincoln Park Zoo
- Frank Lloyd Wright Home and Studio
- Brookfield Zoo
- Museum of Science and Industry
- Willis Tower
- The Beverly Country Club
- Illinois Beach State Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark




