Stayifyoudare - Vacation Rentals in Lakefront Trail

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From $310

         

10.0 (24 Reviews)

Condo

MICH AVE #5|Safe DTown Grant Park, Museums 2bd/2ba

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• South Loop

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From $299

         

|

9.7 (18 Reviews)

Apartment

Luxurious Stay at Modern Apartment with Self Check-in Mins Frm Downtown

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Grand Boulevard

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From $188

         

|

9.0 (7488 Reviews)

Hostel

Hostel ∙ 20 guests

• Air Conditioner
• Parking
• Pool

• Chicago
• The Loop

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From $117

         

|

9.4 (34 Reviews)

House

Mccormick Place Guest House

• Air Conditioner
• Parking
• Balcony/Terrace

• Chicago
• Bronzeville

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From $485

         

10.0 (22 Reviews)

Condo

The Suite Spot Eclectic Modern Central Sleeps 6

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Pilsen

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From $150

         

|

9.0 (1 Review)

Apartment

A Stylish & Cozy Apartment near Downtown Chicago

• Air Conditioner
• Parking
• Child Friendly

• Chicago
• Grand Boulevard

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From $36

         

9.0

Hostel

84 m² Hostel ∙ 4 guests

• 904 ft² Hostel
• Parking
• Pool
• Accessibility

• Chicago
• The Loop

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From $115

         

9.0 (1031 Reviews)

Hostel

HI Chicago Hostel

• Air Conditioner
• Wheelchair Accessible
• Accessibility

• Chicago
• The Loop

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From $221

         

10.0 (22 Reviews)

Condo

Penthouse Condo in Chicago featuring Zero Gravity Massage Chair

• Air Conditioner
• Parking
• TV

• Chicago
• Grand Boulevard

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From $338

         

|

New

Apartment

Mccomick Place/China town getaway

• Parking
• Pet Friendly
• Child Friendly

• Chicago
• Bridgeport

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From $250

         

New

Bed & Breakfast

65 m² Bed and breakfast ∙ 4 guests

• 699 ft² Bed & Breakfast
• Air Conditioner
• Pet Friendly
• TV

• Chicago
• Bridgeport

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From $113

         

8.4 (73 Reviews)

House

Villa Dubois Guest House

• Air Conditioner
• Parking
• Balcony/Terrace

• Chicago
• Bronzeville

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From $447

         

10.0 (21 Reviews)

Apartment

4 #1S - 4 Bedroom/1.5 Bath Condo near McCormick Place, Wintrust Arena

• Parking
• TV
• Security/Safety

• Chicago
• Armour Square

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From $83

         

|

5.0 (2 Reviews)

Apartment

Lit & Trendy 1-Bedroom Apt in the Iconic Hyde Park

• Air Conditioner
• Child Friendly
• Internet

• Chicago
• Hyde Park

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From $263

         

10.0 (18 Reviews)

Apartment

Penthouse, Lux stay near Downtown, McComick & Lake

• Air Conditioner
• Parking
• TV

• Chicago
• North Kenwood

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From $1,582

         

|

10.0 (4 Reviews)

Apartment

Lux Apts with Lake Views and Top Amenities

• Air Conditioner
• Parking
• Pool

• Chicago
• The Loop

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From $671

         

10.0 (14 Reviews)

House

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

• Air Conditioner
• TV
• View

• Chicago
• Hyde Park

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From $884

         

|

10.0 (2 Reviews)

Apartment

Family and Group Friendly 5BR Spacious Unit with Pool Table and Optional Parking Near McCormick Place and Soldier Field

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Near South Side

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From $467

         

10.0 (14 Reviews)

Condo

1 #33 - 4 Bedroom/2 Bath Condo near McCormick Place, Wintrust Arena, Chinatown

• Air Conditioner
• Parking
• TV

• Chicago
• Chinatown

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From $737

         

|

10.0 (2 Reviews)

Apartment

Spacious 6BR Luxury Suite Perfect for Groups Near McCormick Place and Soldier Field

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Near South Side

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From $624

         

10.0 (12 Reviews)

Condo

Dtown Penthouse 3bd VIEWS+Parking +Gym+Pool

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• The Loop

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From $353

         

|

10.0 (2 Reviews)

Apartment

Walkable 2BR Apartment in Chicago South Loop with Optional Parking and Gym Access Near McCormick Place, Museum Campus & Lakefront

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• Near South Side

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From $366

         

10.0 (8 Reviews)

Condo

Downtown MICH AVE #20, Grant Park, Museums 2bd/2ba

• Air Conditioner
• Parking
• Pet Friendly

• Chicago
• South Loop

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From $820

         

10.0 (7 Reviews)

Apartment

Luxéry Stay "Hollywood" Downtown/McCormick/WinTrust Area

• Air Conditioner
• Pet Friendly
• TV

• Chicago
• Near South Side

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★ Pro Tip: Stayifyoudare makes it easy to compare the best listings on Stayifyoudare homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Stayifyoudare 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 Lakefront Trail.