Chicago Rentals
From $90 per night (USD)VRBO
Luxe River North 1BR w/ Pool & Fitness Area, 1 Block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this stylish River North furnished one bedroom apa ...
From $90 per night (USD)VRBO
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Bucktown Loft - top floor, near Bloomingdale Trail
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Unique Bucktown loft studio on the top floor of a restored vintage Chicago building, central to Bucktown & Wicker Park. ...
Click For PricingExpedia
From $485 per night (USD)VRBO
Downtown Penthouse Lake Views #1|Gym, Parking+Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Feel at Home, Unwind, and Enjoy the amenities you deserve at our 2-Story Penthouse with Million $ Views. Guests love st ...
From $485 per night (USD)VRBO
From $193 per night (USD)VRBO
The Chicago Hotel Collection | Comfy Downtown Chicago Stay, Steps from Mag Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $193 per night (USD)VRBO
From $124 per night (USD)VRBO
The Chicago Hotel Collection Magnificent Mile, Stylish Junior King Suite
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $124 per night (USD)VRBO
From $93 per night (USD)VRBO
Upscale Living, Deluxe King, The Chicago Hotel Collection Magnificent Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $93 per night (USD)VRBO
From $187 per night (USD)VRBO
Shop Chicago and Relax by The Bean | City Viwes | 24-hour Gym | 2 Units
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $187 per night (USD)VRBO
From $193 per night (USD)VRBO
City Center, Saint Clair Suite - The Chicago Hotel Collection Magnificent Mile
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $193 per night (USD)VRBO
From $83 per night (USD)VRBO
Windy City Hideaway | Mag Mile Magic | Navy Pier | Pets Allowed
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $83 per night (USD)VRBO
From $93 per night (USD)VRBO
Modern Digs Steps from Mag Mile Shops/Dining with 24-hour Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $93 per night (USD)VRBO
From $94 per night (USD)VRBO
Shop Chicago’s Magnificent Mile – Steps Away from Navy Pier - Bar On-Site
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $94 per night (USD)VRBO
From $200 per night (USD)Expedia
Wrigley/Lakeview Gem- Walk to Wrigley Field/ Parking available!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
GO CUBS GO!! Just renovated and less than a block from iconic Wrigley Field is a cozy 1 BR garden unit. Home to the Cubs ...
From $200 per night (USD)Expedia
From $281 per night (USD)VRBO
Rooms for the Crew | 3 units | Steps to Mag Mile| Navy Pier | 24-hour Gym
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $281 per night (USD)VRBO
From $281 per night (USD)VRBO
The Chicago Hotel Collection Magnificent Mile, Modern Double Queen, 3 Units
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $281 per night (USD)VRBO
From $167 per night (USD)VRBO
The Chicago Hotel Collection Magnificent Mile, Modern Double Queen | 2 Units
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Immerse yourself in the energy of Chicago at our renovated hotel on the Magnificent Mile. Steps from landmarks and luxur ...
From $167 per night (USD)VRBO
From $674 per night (USD)Expedia
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to our beautiful house UChicago campus house in the historic Hyde Park neighborhood of Chicago. This wonderful v ...
From $674 per night (USD)Expedia
From $461 per night (USD)VRBO
Stylish Chicago Retreat: Walk to Loyola University
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Take the trip of a lifetime with friends and family when you stay at this ultimate Chicago getaway! Boasting a sophistic ...
From $461 per night (USD)VRBO
From $966 per night (USD)Expedia
Luxury 6BD/5BTH + Roofdeck - Downtown Chicago!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
This UPSCALE/NEWLY FURNISHED 6 bed and 5 bath building is a perfect oasis for your group! We are steps away from the hea ...
From $966 per night (USD)Expedia
From $176 per night (USD)VRBO
10 minutes to the lake! Family-sized Apt with free parking.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Full kitchen............................................................................................................ ...
From $176 per night (USD)VRBO
From $731 per night (USD)Expedia
Family friendly 5b/ 4ba sun-drenched home in Jefferson Park, 2 car garage!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Our home is perfect for big families, girls trip, wedding parties, & workgroups. We're tucked away in Chicago's Jefferso ...
From $731 per night (USD)Expedia
From $450 per night (USD)VRBO
Chic Urban Retreat Near Wrigley Field w/Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to our stylish 2-bedroom, 2-bathroom condo nestled in the Lakeview/Southport neighborhood, the vibrant heart of ...
From $450 per night (USD)VRBO
From $459 per night (USD)Expedia
Stunning Duplex Retreat 3BR 2BR, Minutes from Downtown Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to your ideal getaway in the lively neighborhoods of Avondale/Logan Square in Chicago, where you'll find our spa ...
From $459 per night (USD)Expedia
From $317 per night (USD)VRBO
Peaceful Cozy Loft | 13 mins DT | 4 mins Lake
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $317 per night (USD)VRBO
From $226 per night (USD)Expedia
Cozy 1-bedroom apartment .luxury building
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This memorable apartment is the perfect home base for your trip to Chicago. Nestled in the heart of the city, this charm ...
From $226 per night (USD)Expedia
From $216 per night (USD)VRBO
Spacious 3 Bedroom Apartment - 10 Minutes to Downtown - Sleeps up to 10
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Spacious 950 sqft 3BR 1BA located 10-15 min from Downtown Tub/Shower Games for adults & kids 4 Smart TVs, free fast wifi ...
From $216 per night (USD)VRBO
From $609 per night (USD)Expedia
Spacious 8 BDRM + 2 Kitchens + Garage! Sleeps 16!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Spacious 8-bedroom townhome withThis newly renovated and styled 8 bedroom in Avondale is ready to host you! Two units ha ...
From $609 per night (USD)Expedia
From $611 per night (USD)VRBO
Single Family Home in Logan w/ 2 Car Garage
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Welcome to our beautiful and spacious home in the trendy Logan Square neighborhood of Chicago! A short 3-minute walk to ...
From $611 per night (USD)VRBO
From $204 per night (USD)VRBO
Elegant King Bed 1.5 Bath Suite in the Heart of Chicago's Gold Coast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Each apartment offers a luxurious living experience, as they come fully furnished with all the amenities you could need. ...
From $204 per night (USD)VRBO
From $414 per night (USD)VRBO
Unique Chicago Penthouse Loft - Amazing Deal & Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Ideal for a Chicago getaway, a business trip, or to visit family & friends! This comfortable 3rd-floor Penthouse Loft (n ...
From $414 per night (USD)VRBO
From $480 per night (USD)VRBO
Spacious Condo w/ Deck ~ 3 Mi to Downtown Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Spend your stay in the Windy City in style at this spacious 3-bedroom, 2-bathroom apartment located just 3 miles from do ...
From $480 per night (USD)VRBO
From $335 per night (USD)VRBO
Large 3 bdrm / dining in the heart of Logan Square mins to DOWNTOWN
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Beautiful, newly renovated three bedroom with one bathroom in the heart of the Logan Square neighborhood of Chicago. Loc ...
From $335 per night (USD)VRBO
From $2368 per night (USD)Expedia
870 bldg - 3 Separate Suites in same building
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 16
Summary: This listing is ideal for LARGE GROUPS that wish to have individual Suites and separate living spaces for diffe ...
From $2368 per night (USD)Expedia
From $177 per night (USD)VRBO
13 mins DT|4 mins Lake | Majestic Modern Style
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
*PEACE* Escape to a serene oasis nestled in the vibrant heart of Uptown, Chicago. Enjoy a fully stocked kitchen, smart T ...
From $177 per night (USD)VRBO
From $224 per night (USD)Expedia
Downtown Park Mich Ave Penthouse - Rooftop & Gym
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at Home, Unwind, and Enjoy the amenities you deserve when you come to Chicago! Guests love staying with us because ...
From $224 per night (USD)Expedia
From $306 per night (USD)VRBO
Fulton market / Noble Square FREE parking, Laundry, 2.5 miles to Mag Mile!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
BEST neighborhood in Chicago. This is the 1st real neighborhood west of all the high-rises, walking distance to restaura ...
From $306 per night (USD)VRBO
From $190 per night (USD)Expedia
Chicago Cityview Chic - Gold Coast/River North
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to our stylish, modern 2-bed, 1-bath condo located in the vibrant Gold Coast/River North neighborhood. Discover ...
From $190 per night (USD)Expedia
From $148 per night (USD)VRBO
Spacious 2BR, this hidden gem combines vintage allure with urban flair!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the charm of The Maestro, an amazing 2-bedroom, 1-bath apartment nestled within a stunning 1920’s era Chicago b ...
From $148 per night (USD)VRBO
From $206 per night (USD)Expedia
A Home Away From Home!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Discover the allure of this newly renovated Georgian house. Boasting ample space for family enjoyment. With its close pr ...
From $206 per night (USD)Expedia
From $187 per night (USD)VRBO
Chic 2BR Haven: Minutes from Downtown & Medical District
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Welcome to your tranquil urban oasis in the vibrant heart of Chicago, IL! Nestled on a serene block near Douglas Park in ...
From $187 per night (USD)VRBO
From $161 per night (USD)Expedia
Classic West Loop 1BR w/ Gym, near Fulton Market & I-90, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this lovely one bedroom Blueground apartment. You’ll love coming h ...
From $161 per night (USD)Expedia
From $289 per night (USD)VRBO
McCormick 2B/2Ba for up to 8 guests with Optional Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $289 per night (USD)VRBO
From $341 per night (USD)Expedia
McCormick Place Skyline view Secret Oasis sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 2 shifts Security o ...
From $341 per night (USD)Expedia
From $446 per night (USD)VRBO
McCormick Luxury 3B/2Ba Corner Oasis for up to 8 guests with optional parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...
From $446 per night (USD)VRBO
From $321 per night (USD)Expedia
McCormick 2B/2Ba for up to 8 guests with Optional Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Amazing City view f ...
From $321 per night (USD)Expedia
From $388 per night (USD)VRBO
420 friendly 3BR/2BA heaven with optional parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $388 per night (USD)VRBO
From $759 per night (USD)Expedia
Luxury Loft Collection 902 - Terrace - River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: BRAND NEW LOFT IN RIVER NORTH! Enjoy your new private luxury loft in Chicago's newest and most luxurious build ...
From $759 per night (USD)Expedia
From $126 per night (USD)VRBO
Deluxe West Loop 1BR w/ Rooftop, Gym & Grills, nr Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this cheery Near West Side furnished one bedroom a ...
From $126 per night (USD)VRBO
From $175 per night (USD)Expedia
Cozy 2 Bedroom unit-15mins Dwtn!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Trendy two unit apartment nested between South Loop and Bronzeville. The unit is in close proximity to McCormick,Winturs ...
From $175 per night (USD)Expedia
From $457 per night (USD)VRBO
McCormick 3B/2Ba Family Oasis up to 8 guests with Parking-Optional/Gym/Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 Queen size beds + ...
From $457 per night (USD)VRBO
From $301 per night (USD)Expedia
McCormick Patio skyline view 2b/2b with optional Parking/sleep 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Private patio • Cit ...
From $301 per night (USD)Expedia
From $499 per night (USD)VRBO
Luxurious McCormick 3be/2ba Suite/up to 8 guests w optional parking/Gym/Patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 3 KING size bedroo ...
From $499 per night (USD)VRBO
From $1076 per night (USD)Expedia
Luxurious McCormick 6 bed/4 bath Suite for up to 12 guests w Jacuzzi/Opt parking
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Jacuzzi in the unit • 2609 sq f Luxurious unit ...
From $1076 per night (USD)Expedia
From $900 per night (USD)VRBO
Luxurious McCormick 5 bed/4 bath Suite for up to 12 guests with optional parking
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Luxurious unit for ...
From $900 per night (USD)VRBO
From $461 per night (USD)Expedia
McCormick Place 6 twin beds + Sofa bed with Optional parking for up to 10 guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • 6 twin size beds + ...
From $461 per night (USD)Expedia
From $799 per night (USD)VRBO
McCormick Place with 5 beds/Pool table/Optional Parking/Sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
• MESSAGE US for SPECIAL RATES • Minutes away from McCormick Place, Wintrust arena, Soldier field • Wabash street locati ...
From $799 per night (USD)VRBO
From $444 per night (USD)Expedia
420 friendly 3BR/2BA heaven with optional parking and sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $444 per night (USD)Expedia
From $763 per night (USD)VRBO
McCormick Pl HUGE 5Br with Pool table/Optional parking/sleeps 12
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $763 per night (USD)VRBO
From $738 per night (USD)Expedia
Luxurious HUGE Penthouse with 4000+ Games, Arcades
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 16
1 of a kind industrial modernist 3000 sq ft designer Penthouse. The Loft stands alone in the building with no neighbors. ...
From $738 per night (USD)Expedia
From $300 per night (USD)VRBO
McCormick Oasis 2br/2ba with Optional Parking/Patio/Gym/sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• MESSAGE US for SPECIAL RATES • McCormick Place only 9 minute walking distance • Access to the Gym • Rooftop access and ...
From $300 per night (USD)VRBO
From $355 per night (USD)Expedia
McCormick Place 3BR/2BA with Optional Parking for up to 8 guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $355 per night (USD)Expedia
From $319 per night (USD)VRBO
McCormick Place 2br/2ba with Optional Parking/Patio/Gym/sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• McCormick Place only 9 minute walking distance • Access to the Gym • Rooftop access and Beautiful patio set up with ou ...
From $319 per night (USD)VRBO
From $452 per night (USD)Expedia
Near McCormick 420 friendly 3br/2ba with Optional Parking/sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $452 per night (USD)Expedia
From $675 per night (USD)VRBO
HUGE 5BR with Optional Parking/Pool table/sleeps 10
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $675 per night (USD)VRBO
From $286 per night (USD)Expedia
McCormick Place 2b/2b with optional parking/sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $286 per night (USD)Expedia
From $269 per night (USD)VRBO
McCormick Place Oasis 2br/2ba with optional Parking/Patio/Gym/sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• MESSAGE US for SPECIAL RATES • McCormick Place only 9 minute walking distance • Access to the Gym • Rooftop access and ...
From $269 per night (USD)VRBO
From $416 per night (USD)Expedia
420 friendly 3BR/2BA heaven with optional parking and sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $416 per night (USD)Expedia
From $301 per night (USD)VRBO
McCormick Place 2br/2ba with optional parking that sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $301 per night (USD)VRBO
From $243 per night (USD)Expedia
420 friendly cutest 1br/1ba with optional parking/sleeps 4
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $243 per night (USD)Expedia
From $302 per night (USD)VRBO
420 friendly 2br/2ba with optional parking / sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $302 per night (USD)VRBO
From $320 per night (USD)Expedia
420 friendly Modern 2BR with optional parking for up to 6 guests
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $320 per night (USD)Expedia
From $424 per night (USD)VRBO
420 friendly 3BR/2BA heaven with optional parking and sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $424 per night (USD)VRBO
From $322 per night (USD)Expedia
McCormick Place 420-Friendly 3BR/2BA with Optional Parking / sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $322 per night (USD)Expedia
From $332 per night (USD)VRBO
McCormick Place 420 friendly 3BR with optional Parking
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
• Smoking inside the unit is allowed • State street location • Minutes walk to McCormick Convention Center • Safe buildi ...
From $332 per night (USD)VRBO
From $656 per night (USD)Expedia
Near McCormick Place 420-Friendly 3BR/2BA with Optional Parking and sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $656 per night (USD)Expedia
From $308 per night (USD)VRBO
McCormick Place Oasis with Optional Parking/Patio/Gym/sleeps 6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
• McCormick Place only 9 min walking distance • Access to the Gym • Private balcony • Rooftop access and Beautiful patio ...
From $308 per night (USD)VRBO
From $361 per night (USD)Expedia
420-Friendly Near McCormick Pl 3BR/2BA with Optional Parking and sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $361 per night (USD)Expedia
From $293 per night (USD)VRBO
McCormick Place 2br/2ba with optional parking and sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $293 per night (USD)VRBO
From $390 per night (USD)Expedia
Near McCormick Place 420- Friendly 3BR/2BA with Optional Parking and Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $390 per night (USD)Expedia
From $317 per night (USD)VRBO
420 friendly beautiful unit with optional parking and sleeps 6
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
During your stay in Downtown Chicago and enjoying the comfort of our sophisticated apartment we will be doing our best t ...
From $317 per night (USD)VRBO
From $261 per night (USD)Expedia
Comfortable Condo in the Heart of Bronzeville by RedAwning
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Discover the perfect blend of elegance and comfort in this beautifully designed condo, located in the heart of Bronzevi ...
From $261 per night (USD)Expedia
From $745 per night (USD)VRBO
East Lincoln Park Gem: Spacious 4BR apartment with modern amenities.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Experience refined living in this garden-level apartment, nestled within a distinguished historic Greystone bui ...
From $745 per night (USD)VRBO
From $638 per night (USD)Expedia
Modern, Luxe, House 20mins to Downtown, Sleeps 16, Private Rooftop, 2car Garage
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 16
Luxurious Modern Retreat with 1000 sqft Rooftop Welcome to the Monticello - our stunning modern new construction, desig ...
From $638 per night (USD)Expedia
From $196 per night (USD)VRBO
Downtown Delight: Chic Stay near Chicago Theater! Pets are welcome!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the Windy City's elegance & charm from our central, downtown location This listing is for a room within a ho ...
From $196 per night (USD)VRBO
From $88 per night (USD)Expedia
Dreamy West Loop 1BR w/ Rooftop & Dog Wash, nr L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one bedroom apartment in Near West Side. It’ll be easy to simply show up and sta ...
From $88 per night (USD)Expedia
From $492 per night (USD)VRBO
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to Bee's Knees - a vintage gem with a Hollywood-glam twist! This 4-BR Chicago bungalow home is the perfect getaw ...
From $492 per night (USD)VRBO
From $196 per night (USD)VRBO
Breath of Fresh Air! Near Willis Tower and Cloud Gate - The Bean, Pet-Friendly
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Experience the Windy City's elegance & charm from our central, downtown location This listing is for a room within a ho ...
From $196 per night (USD)VRBO
From $186 per night (USD)VRBO
Cozy Spacious 3br
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Nice and Spacious Cozy apartment nestled in the heart of chicago, top floor apt. With Double ovens when cooking for a ni ...
From $186 per night (USD)VRBO
From $1278 per night (USD)Expedia
New home w/view & party deck - 2nd Floor
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Prime Location: Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovat ...
From $1278 per night (USD)Expedia
From $1166 per night (USD)VRBO
3Bed/2Bath Wrigley home w/view & party deck 443 ft from Wrigley Field - 3rd Fl
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wrigley Field location directly across from the historical ballpark & Gallagher Way Plaza. Newly renovated down to the s ...
From $1166 per night (USD)VRBO
From $230 per night (USD)Expedia
Rest Easy in the East Village - Quiet Street Only Steps to Top Restaurants, Bars, and Public Transportation by AllSet Turnover
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Stay in the best location in the heart of the East Village/Wicker Park neighborhoods! Located on a quiet tree-lined str ...
From $230 per night (USD)Expedia
From $224 per night (USD)VRBO
3 Bedroom Medical Center!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: A couple house off the popular Taylor St which has plenty of restaurants and bars! The Space: 3 Bedrooms 1 Ful ...
From $224 per night (USD)VRBO
From $439 per night (USD)VRBO
Charming 4BR Coach House in River West Chicago!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Welcome to our stunning 4-bedroom retreat nestled in the heart of Chicago, where urban excitement meets modern ...
From $439 per night (USD)VRBO
From $586 per night (USD)VRBO
Elegant 3-Bed, 3-Bath Home in Chicago <25-minutes to O’Hare & Downtown + Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to this beautifully renovated single-family home, offering luxury, comfort, and modern elegance in the heart of ...
From $586 per night (USD)VRBO
From $238 per night (USD)Expedia
Dalia Flat - Sleeps 10 - 10 minutes to Downtown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 10
Large 3 BR 1BA located 10 min drive from Downtown Chicago Tub/Shower Walking distance from subway/train station Directly ...
From $238 per night (USD)Expedia
From $181 per night (USD)VRBO
Modern Luxury 1bd-1ba - Heart of City: Close to Highway 90 & 94
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Feel comfortable in this spacious and unique 1bd space. New In-law-suite which includes a large family room. There is an ...
From $181 per night (USD)VRBO
From $983 per night (USD)Expedia
Wicker Park Entire House, Private Yard and Parking!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Renovated 4 bed 3 bath home in the heart Wicker Park. PRIVATE FREE PARKING! Incredible backyard with outdoor kitchen and ...
From $983 per night (USD)Expedia
From $244 per night (USD)VRBO
Deluxe River North 1BR w/ Gym, Pool & Roof, nr Riverwalk, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this charming River North furnished one bedroom ap ...
From $244 per night (USD)VRBO
From $151 per night (USD)VRBO
2BD/1 BA with summer patio in quiet Roscoe Village
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to a wonderful home in quiet, family-friendly West Lakeview/Roscoe Village. This is a spacious 2 bedroom+office/ ...
From $151 per night (USD)VRBO
From $95 per night (USD)VRBO
Cozy & Comfy 2 bedroom remodeled with plenty parking
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Welcome to this beautifully remodeled fully furnished apartment for rent located on the south side of Chicago This 2-bed ...
From $95 per night (USD)VRBO
From $396 per night (USD)VRBO
Book the Great Migration Guest House. Family-sized condo near the Green Line.\n\n
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
LOOK FOR THE GREEN DOOR BLACKS IN GREEN LAUNCHES NEXT LEVEL TOURISM IN WOODLAWN In homage to the legendary "Green Boo ...
From $396 per night (USD)VRBO