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Lakes Resorts - Vacation Rentals in Near North Side

Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property! From US $213
         

10.0 (3 Reviews)
Resort
Explore Chicago! Free Breakfast, Fully-equipped Kitchen, Pet-friendly Property!
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Luxury Places to Stay in Near North Side

Over 1193+ Luxury Places to Stay in or Near Near North Side
Spectacular Gilded Age 6 Bedroom Gold Coast Mansion with Deck From US $3,466
         

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New
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Spectacular Gilded Age 6 Bedroom Gold Coast Mansion with Deck
  • Air Conditioner
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  • Pet Friendly

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Chicago Gold Coast Luxury Home Best Location walking distance to anywhere! From US $2,932
         

10.0 (25 Reviews)
House
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
  • Air Conditioner
  • Parking
  • Pet Friendly

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The Orleans - Entire Building - With Rooftop Deck! From US $2,925
         

New
Apartment
The Orleans - Entire Building - With Rooftop Deck!
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Luxurious Old Town Chicago Suites – Perfect for Families & Corporate Stays From US $2,883
         

New
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Luxurious Old Town Chicago Suites – Perfect for Families & Corporate Stays
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Gather Your Group: 20BRs in Lincoln Park From US $2,785
         

New
Apartment
Gather Your Group: 20BRs in Lincoln Park
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Ideal Lincoln Park Getaway for Large Groups From US $2,318
         

New
Apartment
Ideal Lincoln Park Getaway for Large Groups
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Luxury Loft Collection 1, 2, 3 From US $2,301
         

New
Apartment
Luxury Loft Collection 1, 2, 3
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The Orleans - Floor 2 Private roof deck Patio! From US $2,189
         

10.0 (1 Review)
Apartment
The Orleans - Floor 2 Private roof deck Patio!
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Top-Rated Vacation Rentals with a Pool in Near North Side

Over 399+ Top-Rated Vacation Rentals with a Pool in or Near Near North Side
LOCATION! 2b/2b Condo, 51st Floor AMAZING Views, Pool and other Amenities! From US $215
         

10.0 (24 Reviews)
Condo
LOCATION! 2b/2b Condo, 51st Floor AMAZING Views, Pool and other Amenities!
  • Air Conditioner
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  • Pool

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Best Location! Luxury 51st FL Amazing Views of Lake & City, Hotel-like Amenities From US $303
         

10.0 (12 Reviews)
Condo
Best Location! Luxury 51st FL Amazing Views of Lake & City, Hotel-like Amenities
  • Air Conditioner
  • Parking
  • Pool

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Luxury Designer Penthouse West |Pool| Gold Coast From US $516
         

10.0 (9 Reviews)
Apartment
Luxury Designer Penthouse West |Pool| Gold Coast
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53-54 Floor Penthouse From US $610
         

10.0 (7 Reviews)
Apartment
53-54 Floor Penthouse
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Luxury Meets Fun: Downtown PH w/Private Game Room From US $639
         

10.0 (5 Reviews)
Apartment
Luxury Meets Fun: Downtown PH w/Private Game Room
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  • Pool
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2BR Retreat in Downtown + City Skyline Views From US $491
         

10.0 (3 Reviews)
Apartment
2BR Retreat in Downtown + City Skyline Views
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Elegant 2BR with Resort Amenities & City Views From US $470
         

10.0 (3 Reviews)
Apartment
Elegant 2BR with Resort Amenities & City Views
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  • Pool
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2BR near Riverwalk + downtown access From US $429
         

10.0 (3 Reviews)
Apartment
2BR near Riverwalk + downtown access
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Pet-Friendly Vacation Rentals in Near North Side

Over 552+ Pet-Friendly Vacation Rentals in or Near Near North Side
Luxury Loft Collection 703 - Terrace - River North From US $575
         

10.0 (21 Reviews)
Apartment
Luxury Loft Collection 703 - Terrace - River North
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Foundry Unmatched Skyline Views at Lincoln Park From US $376
         

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9.4 (11 Reviews)
Apartment
Foundry Unmatched Skyline Views at Lincoln Park
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ENVITAE Hotel 4 Bedroom Luxury Apartments From US $1,233
         

10.0 (8 Reviews)
Hotel
ENVITAE Hotel 4 Bedroom Luxury Apartments
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Luxury Loft Collection 02 - Terrace - River North From US $569
         

10.0 (20 Reviews)
Apartment
Luxury Loft Collection 02 - Terrace - River North
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Luxury Loft Collection 903 - Terrace - River North From US $591
         

10.0 (7 Reviews)
Apartment
Luxury Loft Collection 903 - Terrace - River North
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Luxury Designer Penthouse|Private Deck|Gold Coast From US $480
         

10.0 (7 Reviews)
Apartment
Luxury Designer Penthouse|Private Deck|Gold Coast
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  • Pet Friendly

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Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces From US $1,151
         

10.0 (6 Reviews)
House
Gilded Age Gold Coast Mansion with Parking, Deck, Fireplaces
  • Air Conditioner
  • Parking
  • Pet Friendly

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Gold Coast Living: Modern Studio Unit From US $176
         

10.0 (4 Reviews)
Apartment
Gold Coast Living: Modern Studio Unit
  • Pet Friendly
  • TV
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Large Vacation Homes & Villas in Near North Side

Over 138+ Large Vacation Homes & Villas in or Near Near North Side
Magic Factory Loft 2East 4 Bd/3 Ba Families Groups From US $822
         

10.0 (119 Reviews)
Apartment
Magic Factory Loft 2East 4 Bd/3 Ba Families Groups
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Post Chicago Getaway Ideal 4BR for Groups From US $751
         

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9.2 (15 Reviews)
Apartment
Post Chicago Getaway Ideal 4BR for Groups
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Magic Factory Loft 3East 4 Bd/4 Ba Families Groups From US $1,119
         

10.0 (106 Reviews)
Apartment
Magic Factory Loft 3East 4 Bd/4 Ba Families Groups
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City Center, River North Condo HUGE 3BR, Patio, Parking(2x) From US $773
         

10.0 (30 Reviews)
Apartment
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
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Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago From US $488
         

10.0 (9 Reviews)
Apartment
Modern Apartment with Private Rooftop Patio & Free Parking in Downtown Chicago
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Spacious 4BR Central Apartment w/Skyline Views From US $380
         

10.0 (7 Reviews)
Apartment
Spacious 4BR Central Apartment w/Skyline Views
  • Air Conditioner
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  • Wheelchair Accessible

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Luxury Loft Collection COMBO 02/03 | Terrace From US $1,147
         

10.0 (2 Reviews)
Apartment
Luxury Loft Collection COMBO 02/03 | Terrace
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Luxury Loft Collection COMBO 902/903 Terrace From US $1,084
         

10.0 (2 Reviews)
Apartment
Luxury Loft Collection COMBO 902/903 Terrace
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  • Pet Friendly

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Wheelchair Accessible Vacation Homes in Near North Side

Over 873+ Wheelchair Accessible Vacation Homes in or Near Near North Side
Downtown Guild #3 | Mag Mile Gold Coast The Lake! From US $200
         

10.0 (21 Reviews)
Condo
Downtown Guild #3 | Mag Mile Gold Coast The Lake!
  • Air Conditioner
  • TV
  • Wheelchair Accessible

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Luxurious Haven in the Heart of Chicago! [32 Day+] From US $191
         

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New
Apartment
Luxurious Haven in the Heart of Chicago! [32 Day+]
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3BR New Modern Lux City Escape From US $453
         

10.0 (3 Reviews)
Hotel
3BR New Modern Lux City Escape
  • Air Conditioner
  • Wheelchair Accessible
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River North Private Balcony With In and Out Parking From US $292
         

10.0 (3 Reviews)
Apartment
River North Private Balcony With In and Out Parking
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Lincoln Park Getaway: Skyline Views & Luxury From US $433
         

10.0 (2 Reviews)
Apartment
Lincoln Park Getaway: Skyline Views & Luxury
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  • Pool
  • TV

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Prime Lincoln Park Views + Modern Amenities Await From US $420
         

10.0 (2 Reviews)
Apartment
Prime Lincoln Park Views + Modern Amenities Await
  • Air Conditioner
  • Pool
  • TV

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Luxury Designer Penthouse Combo West | Gold Coast From US $967
         

10.0 (1 Review)
Apartment
Luxury Designer Penthouse Combo West | Gold Coast
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Downtown Gold Coast 4bd/4ba - 2 apts From US $837
         

10.0 (1 Review)
Apartment
Downtown Gold Coast 4bd/4ba - 2 apts
  • Air Conditioner
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  • Wheelchair Accessible

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Near North Side Varoom and Airbnb Places to Stay Under $200

Over 451+ Near North Side Varoom and Airbnb Places to Stay Under $200
Chic 1-bedroom condo in the heart of Chicago, next to Mag Mile From US $143
         

10.0 (2 Reviews)
Condo
Chic 1-bedroom condo in the heart of Chicago, next to Mag Mile
  • Air Conditioner
  • Pool
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Streeterville Studio w Gym Pool nr Navy Pier CHI-445 From US $197
         

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New
Apartment
Streeterville Studio w Gym Pool nr Navy Pier CHI-445
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Residence Inn Chicago Downtown Magnificent Mile From US $168
         

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9.6 (401 Reviews)
Hotel
Residence Inn Chicago Downtown Magnificent Mile
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Chicago Cityview Chic - Gold Coast/River North From US $199
         

10.0 (1 Review)
Condo
Chicago Cityview Chic - Gold Coast/River North
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Trendy Streeterville Studio w/Pool & Gym, nr Navy Pier, by Blueground From US $176
         

10.0 (1 Review)
Apartment
Trendy Streeterville Studio w/Pool & Gym, nr Navy Pier, by Blueground
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  • Pet Friendly
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Sleek 1BR Apt w/Laundry From US $159
         

10.0 (1 Review)
Apartment
Sleek 1BR Apt w/Laundry
  • Pet Friendly
  • TV
  • Wheelchair Accessible

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Sleek River North 1BR w/Gym, Lounge & Roof, 1 block to L, by Blueground From US $150
         

10.0 (1 Review)
Apartment
Sleek River North 1BR w/Gym, Lounge & Roof, 1 block to L, by Blueground
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  • Pet Friendly
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Deluxe River North 1BR w/Gym, Lounge & Roof, nr Riverwalk, by Blueground From US $126
         

10.0 (1 Review)
Apartment
Deluxe River North 1BR w/Gym, Lounge & Roof, nr Riverwalk, by Blueground
  • Air Conditioner
  • Pet Friendly
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Instantly Bookable Vacation Homes in Near North Side

Over 752+ Instantly Bookable Vacation Homes in or Near Near North Side
Brilliant Downtown Chicago 3-Bedroom Condominium From US $416
         

10.0 (50 Reviews)
Condo
Brilliant Downtown Chicago 3-Bedroom Condominium
  • Air Conditioner
  • TV
  • Balcony/Terrace

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Twice as Nice: Chic 2BR Stay with Style & Space From US $266
         

9.0 (2 Reviews)
Apartment
Twice as Nice: Chic 2BR Stay with Style & Space
  • Air Conditioner
  • Pet Friendly
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Gorgeous 3BR River North Condo - Free Parking From US $683
         

10.0 (29 Reviews)
Condo
Gorgeous 3BR River North Condo - Free Parking
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The Orleans Floor 3 Private rooftop deck! From US $2,097
         

10.0 (1 Review)
Apartment
The Orleans Floor 3 Private rooftop deck!
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Designer Loft 2E | Heart of Gold Coast/River North From US $527
         

10.0 (1 Review)
Apartment
Designer Loft 2E | Heart of Gold Coast/River North
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5-Star Gold Coast Experience in a Luxe 2BR Retreat From US $453
         

10.0 (1 Review)
Apartment
5-Star Gold Coast Experience in a Luxe 2BR Retreat
  • Air Conditioner
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Historic Charm & Modern Luxury in Chicago’s Iconic Old Town - Stay Level! From US $395
         

10.0 (1 Review)
Apartment
Historic Charm & Modern Luxury in Chicago’s Iconic Old Town - Stay Level!
  • Air Conditioner
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Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife From US $356
         

10.0 (1 Review)
Apartment
Stylish River North Suites Luxe Comfort Near Chicago’s Best Shopping & Nightlife
  • Air Conditioner
  • Parking
  • Pet Friendly

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About Near North Side Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Lakesresorts Near North Side, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Near North Side. Places to stay near Near North Side are 450 ft² on average, with prices averaging $213 a night.

Lakesresorts makes it easy and safe to find and compare vacation rentals in Near North Side with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Near North Side

Type Count
Resorts 1

Use these Quick Filters to Find a Vacation Rental in Near North Side

★ Pro Tip: Lakesresorts makes it easy to compare the best listings on Lakesresorts homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Lakesresorts homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Near North Side.

Weather in Near North Side

View the weather forecast for Near North Side before booking your Near North Side Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay Near Near North Side, IL


Goose Island 4,305 Properties Legacy Motors Automotive Art Gallery 4,265 Properties Pump It Up Party Zone 4,253 Properties Judy A Saslow Gallery 4,211 Properties ArchiTech Gallery 4,205 Properties Magnificent Mile 3,906 Properties Michigan Avenue 3,869 Properties River North 314 Properties Streeterville 152 Properties Rush and Division 83 Properties Gold Coast 38 Properties Killgubbin 31 Properties

Complexes around Near North Side, IL


Wells Apartments St Chicago 132 Properties Kasa River North 12 Properties Gold Coast Doorman Blocks 9 Properties Town 9 Properties Claridge 3 Properties Courtyard 3 Properties Flat 3 Properties The Whitehall Hotel 2 Properties Sonder Cros 1 Properties