
Holiday houses in Near North Side
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Top-rated holiday rentals in Near North Side
Guests agree: these stays are highly rated for location, cleanliness and more.

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom
Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Oldtown Stylish cute studio Near Gold Coast
Welcome to our stylish studio unit nestled in the heart of the city's charming old town area! This cozy space is perfect for solo travelers or couples seeking a comfortable retreat. The studio boasts a spacious bathroom, providing ample room for relaxation after a day of exploring.With its central location, you'll have easy access to the city's vibrant attractions, trendy cafes, and historic landmarks. Our studio unit offers the perfect blend of convenience and comfort for your stay in the city.

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!

Sunny full floor (Sleeps 4+ guests)
A whole floor to yourself — the floor is entirely/ exclusively yours! Full floor finished basement w/ light from glass sliding doors, 1.5 private bedrooms, and 2 desks. Spic & span - steamed cleaned after every guest! New memory foam regular queen size bed w/ 2 more queen size airbeds (per request). 7 mins by car to downtown or 2 blocks to train station/ bus stop that both go into downtown. Street level parking available. Masks are optional, not required. Chicago Registration #: R21000069179

Upscale High-Rise Apt · Rooftop Pool + Views
Stay in this brand-new 2025 apartment with luxury amenities. Perfect for work or leisure, it offers everything you need for a comfortable stay. Building Amenities: - 24/7 concierge & secure entry - Rooftop pool & gym with skyline views - Rooftop lounge with a fireplace - Steps from grocery stores & restaurants - Paid parking nearby Unit Highlights: - Stunning views of the city - Work from home space - In-unit washer & dryer - Fully equipped kitchen - Fast WiFi - Modernly designed interior

Winter Escape• Modern 1BR • Walk to All
Prime Location: Lincoln Park Zoo, Lake Michigan, North Avenue Beach, top-rated local restaurants, cafés, and boutiques Spacious & Bright: Enjoy a large open living space with natural light Work-Friendly: Dedicated workspace and fast Wi-Fi, ideal for remote work or study Self Check-in w/ Secure Entry: Keypad code access Easy Transit: Close to CTA buses and trains for fast access to downtown, Wrigley Field, and more FREE to use washer/ dryer with detergents and cleaning supplies

Chic retreat near the best of Lakeview & Wrigley
Stylish, centrally-located getaway perfect for a visit to the Windy City! This charming space was freshly renovated in early 2022 with ample space (nearly 1500 sq ft), a Peloton exercise bike, and kitchenette. Located in the trendy Southport Corridor blocks from the best of Chicago's north side; shopping, fine dining, bars, Wrigley Field, close to Brown line train public transit with Whole Foods at the end of the block!

Cabin 206 at 747 Lofts
This studio apartment is in the perfect location in Chicago for getting to Downtown via the Blue Line L or to the Hot West Loop and Randolph street restaurant row. Walk to bars, shops, restaurants, coffee liquor stores and transportation with ease! You will love our spa baths, in unit laundry and full modern kitchens to make it feel like a home away from home. One of the best pizza spots in Chicago is only steps away!

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.

Garden on Warren
Near West Side / West Loop location, less than 10 minute walk to United Center for Blackhawks, Bulls, music, concerts, shows, and events. Close proximity to CTA Pink & Green lines, Union Park, Randolph & Fulton Street dining districts, University of Illinois at Chicago and Rush Medical District. Private entry, very secure and quiet apartment.

Great Location Studio II
Great location studio in the Gold Coast. Close to many attractions Chicago has to offer 5 min walk to Oak st. Beach & Magnificent Mile, 5 min to John Hancock tower, 5 min red line/brown line. 10 min walk to MCA, 20 min to Millenium Park and Art Institute.. Hardwood floor, full size bed. Maximum occupancy 2 persons.
Popular amenities for Near North Side holiday rentals
Other great holiday rentals in Near North Side

Cozy Room/Fast Wi-fi/94 Walk Score/Desk/Wash/Dryr

Comfortable Private 1 bedroom

Bees Knees - Room 3

Unique River North Loft. Middle Room

Private, dog-friendly room near downtown Chicago

i2-Right in front United Center&Next to Downtown

Playful spirit and sustainable practices

T12- Room - 15 min to Red Line
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 | $277 NZD | $283 NZD | $303 NZD | $342 NZD | $442 NZD | $509 NZD | $478 NZD | $455 NZD | $401 NZD | $366 NZD | $353 NZD | $307 NZD |
| 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 holiday rentals in Near North Side

Total holiday rentals
Explore 1,670 holiday rentals in Near North Side

Nightly prices starting at
Near North Side holiday rentals start at $17 NZD per night before taxes and fees

Verified guest reviews
Over 47,750 verified reviews to help you choose

Family-friendly holiday rentals
590 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 910 rentals that welcome pets

Holiday rentals with a pool
780 properties feature pools

Rentals with dedicated workspaces
900 properties have a dedicated workspace

Wi-Fi availability
1,650 of Near North Side holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Near North Side rentals

4.7 Average rating
Near North Side stays receive an average rating of 4.7 out of 5 from guests

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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- Family-friendly rentals Near North Side
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- Rentals with pools Near North Side
- 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
- The Field Museum
- Oak Street Beach
- Wicker Park
- Lincoln Park Zoo
- Garfield Park Conservatory
- Frank Lloyd Wright Home and Studio
- The Beverly Country Club
- Museum of Science and Industry
- Brookfield Zoo
- Willis Tower
- Illinois Beach State Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark




