Cook Area Rentals
- From $319 per night (USD)
VRBO
Downtown Penthouse Vintage Loft Pvt Balcony+Gym
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 7
Welcome to our Penthouse Loft in the heart of Downtown! Guests love our home because: -It's Unique! -High loft ceilings ...
From $319 per night (USD)VRBO
- From $140 per night (USD)
Expedia
Top floor of Historic Oak Park Home \/ 2 Car Grge
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Secluded but never isolated; 3 blocks from the L-line, next door to Hemingway's birthplace, surrounded by dozens of Fran ...
From $140 per night (USD)Expedia
- From $173 per night (USD)
VRBO
Stylish Luxe King bed w\/Free Parkng near DT Oak Pk
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This gorgeous 2bed/2bath packs a powerful punch, and more amenities than you'll know what to do with. -1 Private Parkin ...
From $173 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Everthing Illinois has to offer at Your Arms Reach! Onsite Dining, Free Parking
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $124 per night (USD)VRBO
- From $262 per night (USD)
VRBO
Chicago's Hidden Treasure \"Evanston, IL\" Urban Luxury with comfort
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Eco-Friendly, modern, sleek, condo with modern finishes and a sweeping Terrace and resort-like amenities are just steps ...
From $262 per night (USD)VRBO
- From $262 per night (USD)
VRBO
Half a mile from everything in the heart of Evanston, Illinois
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Northwestern Alumni, Disney + Fans, Neflix Aficionado, Parents, Corporate Travelers, and Evanston Adventure Seekers!! T ...
From $262 per night (USD)VRBO
- From $247 per night (USD)
VRBO
Your Illinois Adventure Awaits! 2 Affordable Units, Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $247 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Just What You Were Looking For! Free Parking, Restaurant, Near Odyssey Fun World
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $124 per night (USD)VRBO
- From $247 per night (USD)
VRBO
Short Drive from Downtown! 2 Comfortable Units, Free Parking, Onsite Dining!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $247 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Matteson Awaits! Free Parking, Dining, Short Drive to Odyssey Fun World!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $124 per night (USD)VRBO
- From $371 per night (USD)
VRBO
Look No Further! 3 Family-friendly Units, Onsite Restaurant, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $371 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Experience Matteson Like Never Before! Restaurant, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $124 per night (USD)VRBO
- From $247 per night (USD)
VRBO
Friends Getaway! 2 Family-friendly Units, Onsite Restaurant, Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $247 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Comfort & Convenience Awaits! Family-friendly, Free Parking, Onsite Restaurant
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $124 per night (USD)VRBO
- From $371 per night (USD)
VRBO
Everything You Need for Your Illinois Trip! 3 Classy Units, Free Parking, Dining
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $371 per night (USD)VRBO
- From $371 per night (USD)
VRBO
Everthing Matteson has to offer at Your Arms Reach! 3 Great Units, Free Parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $371 per night (USD)VRBO
- From $247 per night (USD)
VRBO
Right On Your Budget! 2 Great Units, Onsite Dining, Free Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $247 per night (USD)VRBO
- From $491 per night (USD)
VRBO
Perfect Staycation! 4 Family-friendly Units, Free Parking, Dining
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $491 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Prime Matteson Location! Onsite Restaurant and Bar, Free Parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $124 per night (USD)VRBO
- From $247 per night (USD)
VRBO
2 Great Units, Free Parking, Dining, Minutes to Hollywood Casino Amphitheater!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $247 per night (USD)VRBO
- Click For Pricing
VRBO
Nice 3 bedroom fully loaded
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 1
Nice place on a very quite block, The house has plenty space Clean and sterilize. It has all Amenities to make it a very ...
Click For PricingVRBO
- From $124 per night (USD)
VRBO
Bright Medical District 2BR w\/ Gym + W\/D, 1 block to L, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two-bedroom Medical District apartment with high floor views over the city. It’l ...
From $124 per night (USD)VRBO
- From $314 per night (USD)
VRBO
❤️ Spacious and Airy Apartment With Parking On Site!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to Chicago! We're located 15 minutes from downtown Chicago, located in the Uptown neighborhood, near restaurants ...
From $314 per night (USD)VRBO
- From $204 per night (USD)
VRBO
Fun and Stylish 3BR in Logan Square! Near Wrigleyville!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Welcome to Chicago! Whether you’re in town to seal a business deal or have a short holiday breather, our warm three-be ...
From $204 per night (USD)VRBO
- From $113 per night (USD)
VRBO
Bright Loop 1BR w\/ Gym, Pool, nr. Financial District, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cheery one-bedroom Blueground apartment. You’ll love coming h ...
From $113 per night (USD)VRBO
- From $86 per night (USD)
VRBO
Sizeable Lakeview 2BR, walk to L, Wrigleyville district, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Show up and start living from day one in Chicago with this pretty two-bedroom Blueground apartment. You’ll love coming h ...
From $86 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Gorgeous Loop 1BR w\/ Gym, Pool, near Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this bright The Loop furnished one-bedroom apartme ...
From $124 per night (USD)VRBO
- From $110 per night (USD)
VRBO
Gorgeous Loop 1BR w\/ Pool, Gym, nr. Financial District by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Feel at home wherever you choose to live with Blueground. You’ll love this sophisticated West Loop furnished one-bedroom ...
From $110 per night (USD)VRBO
- From $344 per night (USD)
VRBO
Woodlawn Oasis...10 Minutes to Dining & Downtown
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 12
Fun times with family and friends at this stylish beautiful home located 10 mins from Hyde Park, (Tiger Woods) Golf Cour ...
From $344 per night (USD)VRBO
- From $194 per night (USD)
Expedia
The Comfy King Ranch \/King Bed\/Fast WiFi & Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
This beautiful, newly remodeled, spacious, 3 bedroom 2 bath ranch style home is set back on a large lot. Its located clo ...
From $194 per night (USD)Expedia
- From $1027 per night (USD)
VRBO
The Inn at Wrigleyville, Beautiful New 4 Bedroom Sleeps 9
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to the Wrigleyville Inn, where you can catch a fly ball from our front porch! Recently built from the ground up ...
From $1027 per night (USD)VRBO
- From $491 per night (USD)
VRBO
Affordable Matteson Getaway! 4 Convenient Units, Onsite Dining, Free Parking
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $491 per night (USD)VRBO
- From $491 per night (USD)
VRBO
Dream Illinois Getaway! 4 Comfortable Units, Free Parking, Onsite Dining
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 16
This suburban Chicago property offers budget-friendly accommodations and convenience, just a short drive from downtown. ...
From $491 per night (USD)VRBO
- From $145 per night (USD)
VRBO
The Monroe House - Just blocks from the CTA and 20 minutes from downtown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This newly remodeled space is an elegant retreat featuring 10 foot ceilings, local art treasures and plush linens. Our ...
From $145 per night (USD)VRBO
- From $201 per night (USD)
VRBO
Roscoe Village- Only steps to cute shops & dining! Sleeps 4-6
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your home away from home nestled in the Village within the City – Roscoe Village in Chicago, IL. Roscoe Vil ...
From $201 per night (USD)VRBO
- From $324 per night (USD)
VRBO
Kasa | Bright & Airy 2 BD + Fast Wifi | River North Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $324 per night (USD)VRBO
- From $294 per night (USD)
VRBO
Kasa | Modern Studio + Rooftop Sundeck | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $294 per night (USD)VRBO
- From $288 per night (USD)
VRBO
Kasa | Stylish Studio + Gym Access | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $288 per night (USD)VRBO
- From $279 per night (USD)
VRBO
Kasa | Relaxing Studio + Laptop Friendly | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $279 per night (USD)VRBO
- From $356 per night (USD)
VRBO
Kasa | Modern 1 BD + Pool Access |River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $356 per night (USD)VRBO
- From $227 per night (USD)
VRBO
Kasa | Modern Studio + Near the Magnificent Mile | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $227 per night (USD)VRBO
- From $262 per night (USD)
VRBO
Kasa | Bright & Airy Studio + Pool Access | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $262 per night (USD)VRBO
- From $296 per night (USD)
VRBO
Kasa | Fresh & Bright Studio + Pet Friendly | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $296 per night (USD)VRBO
- From $349 per night (USD)
VRBO
Kasa | Welcoming 1 BD + Gym Access | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $349 per night (USD)VRBO
- From $222 per night (USD)
VRBO
Kasa | Inviting Studio + Rooftop Sundeck | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $222 per night (USD)VRBO
- From $294 per night (USD)
VRBO
Kasa | Inviting Studio + Pet Friendly | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $294 per night (USD)VRBO
- From $189 per night (USD)
VRBO
Kasa | Welcoming Studio + Near Upscale Eateries | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $189 per night (USD)VRBO
- From $382 per night (USD)
VRBO
Kasa | Fresh & Bright 2 BD + Laptop Friendly | River North Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $382 per night (USD)VRBO
- From $278 per night (USD)
VRBO
Kasa | Comfy Studio + Fast Wifi | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 0
- Sleeps:
- 2
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $278 per night (USD)VRBO
- From $380 per night (USD)
VRBO
Kasa | Inviting 1 BD + Pet Friendly | River North Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: Halfway between Old Town and River North, our Kasa offers comfort, class, and convenience. Situated in a brand ...
From $380 per night (USD)VRBO
- From $185 per night (USD)
VRBO
Schaumburg\/Woodfield. Entire house for the whole family. 3 bedrooms.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Licensed Short Term Rental 3-bedroom 1.5 bath ranch house, located in a very quiet safe beautiful neighborhood of Schaum ...
From $185 per night (USD)VRBO
- From $346 per night (USD)
VRBO
Kasa | Comfy 2 BD + Gym Access | Chicago
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Summary: It’s easy to get a taste of Chicago’s culture and cuisine at Kasa South Loop Chicago, located within walking di ...
From $346 per night (USD)VRBO
- From $244 per night (USD)
VRBO
The NICEST place in Evanston for Families 1500Main
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
No Additional Cleaning Fee! --- Fully Furnished 2-story, 2 bedroom attached Townhouse/Duplex with a new King bed in th ...
From $244 per night (USD)VRBO
- From $222 per night (USD)
VRBO
The Bright Retreat in Andersonville
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark St ...
From $222 per night (USD)VRBO
- From $36 per night (USD)
VRBO
Fully furnished bedroom near medical district\/UIC
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 1
Recently renovated and great location for this duplex apartment with central air/heat and in-unit washer & dryer! Room i ...
From $36 per night (USD)VRBO
- From $728 per night (USD)
VRBO
811 PHA - Stunning Penthouse - Downtown River North
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 13
Absolutely stunning penthouse in a BRAND NEW BUILDING downtown with spectacular city view from your very own private roo ...
From $728 per night (USD)VRBO
- From $565 per night (USD)
VRBO
Best location downtown - River North near Mag Mile
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: This is a super unique place! This Downtown Living destination is perfect for everything from families with sma ...
From $565 per night (USD)VRBO
- From $1414 per night (USD)
VRBO
870 BLDG- Downtown Living - Entire Building - Sleeps 34!!
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 34
This listing is ideal for LARGE GROUPS that wish to have individual Suites and separate living spaces for different grou ...
From $1414 per night (USD)VRBO
- From $525 per night (USD)
VRBO
858 3S - Luxury Downtown Penthouse with Private Rooftop!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
BRAND NEW 2020 REMODEL BUILT SPECIFICALLY FOR AIRBNB!! The entire property is designed by a famous Chicago Designer usi ...
From $525 per night (USD)VRBO
- From $189 per night (USD)
Expedia
Charming Home with Hot Tub and Private Yard. RELAX and be at PEACE
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
A Rare gem in the heart of Homewood. This 2-bedroom remodeled home is charming, sophisticated and discrete. It is minut ...
From $189 per night (USD)Expedia
- From $511 per night (USD)
VRBO
One-of-a-Kind Stylish 4BD Home near United Center
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Unique and lovingly curated design choices greet you from the moment you step through the front door of our three level ...
From $511 per night (USD)VRBO
- From $360 per night (USD)
VRBO
McCormick Place 2b\/2b family unit with optional parking for up to 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Amazing City view f ...
From $360 per night (USD)VRBO
- From $350 per night (USD)
VRBO
McCormick Place Skyline view 2br\/2ba with optional parking for up to 6 guests
- 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 $350 per night (USD)VRBO
- From $602 per night (USD)
VRBO
McCormick Place Spacious corner 3br\/2b with optional parking for up to 8 guests
- 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 $602 per night (USD)VRBO
- From $194 per night (USD)
VRBO
The Avondale Guesthouse
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This is a private three bedroom house you will be reserving in the Avondale neighborhood. Plenty of available free stree ...
From $194 per night (USD)VRBO
- From $469 per night (USD)
VRBO
McCormick Place Luxurious 3br\/2ba family heaven with optional parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • City skyline view • ...
From $469 per night (USD)VRBO
- From $118 per night (USD)
VRBO
Stunning Logan Square 2BR w\/ Roof Deck & Gym, 1 block to L, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two-bedroom Logan Square apartment with balcony views over the city. It’ll be ea ...
From $118 per night (USD)VRBO
- Click For Pricing
VRBO
Kasa | Get Some Air on Your Balcony | Chicago
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Summary: With Oak Street Beach, Michigan Avenue, and Gold Coast all within walking distance, Our Kasas are well-connecte ...
Click For PricingVRBO
- From $180 per night (USD)
VRBO
MODERN-SLEEK-BRIGHT Avondale Apartment...Ideal Northside Location
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This well appointed 2 bedroom and 1.5 bathroom apartment is the ideal place to stay in Chicago’s Northside. It’s perfec ...
From $180 per night (USD)VRBO
- From $829 per night (USD)
VRBO
Across From Wrigley Field, Beautiful New 4 Bedroom Featured On Travel Channel!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Located inside one of the iconic Wrigley Rooftops, and just a few steps away from Wrigley Field, this apartment offers a ...
From $829 per night (USD)VRBO
- From $300 per night (USD)
VRBO
NEW LUXURY PENTHOUSE CONDO
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 9
OVERVIEW: This is a spacious penthouse condo with an amazing city skyline view on private rooftop terrace. Comfortably s ...
From $300 per night (USD)VRBO
- From $119 per night (USD)
Expedia
\"The Estates\" 2 PRIVATE BEDROOMS in our Home, Hot Tub\/Bathrooms & More
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
PRIVATE ROOMS IN OUR HOME AS WE LIVE IN THE PROPERTY. NOT ENTIRE HOUSE!!! The “Estates” is an affordable place with ...
From $119 per night (USD)Expedia
- From $260 per night (USD)
VRBO
The Country Life - house
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 14
The Country life is a beautiful suburban home just 20 minute from Chicago. The entire house is yours to take in this pea ...
From $260 per night (USD)VRBO
- From $392 per night (USD)
VRBO
McCormick Place Stylish corner unit with optional parking for up to 6 guests
- 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 $392 per night (USD)VRBO
- From $1266 per night (USD)
VRBO
THE COMPOUND Large Exquisite House Private Yard ''Best Location'' Well Appointed
- Bedrooms:
- 7
- Bathrooms:
- 5
- Sleeps:
- 28
Welcome to The Compound! Walk to everything Chicago has to offer- downtown, beach, park, restaurants and bars; bring fam ...
From $1266 per night (USD)VRBO
- From $165 per night (USD)
VRBO
Serene Arlington Heights 2BR w\/ Gym & W\/D, easy commute, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Feel at home wherever you choose to live with Blueground. You’ll love this charming Arlington Heights furnished two-bedr ...
From $165 per night (USD)VRBO
- From $124 per night (USD)
VRBO
Premium Arlington Heights 1BR w\/ Gym & W\/D, near Metra, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cozy one-bedroom Blueground apartment. You’ll love coming hom ...
From $124 per night (USD)VRBO
- From $95 per night (USD)
VRBO
Sleek Arlington Heights 1BR w\/ Gym & Lounge, near Metra, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this cheery one-bedroom Blueground apartment. You’ll love coming h ...
From $95 per night (USD)VRBO
- From $147 per night (USD)
VRBO
Stellar Arlington Heights 2BR w\/ Gym & Dog Spa, near Metro, by Blueground
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Discover the best of Chicago, with this two-bedroom Arlington Heights apartment with views over the city. It’ll be easy ...
From $147 per night (USD)VRBO
- From $480 per night (USD)
VRBO
Stunning Corner 2BR in the Loop | City & Lake Views
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Summary: Dramatic 1,250+ square foot corner apartment with 12 foot tall ceilings, massive windows, and panoramic city an ...
From $480 per night (USD)VRBO
- From $621 per night (USD)
VRBO
Spectacular Corner 3BR in the Loop | City Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Stylish 1,400+ square foot corner apartment with 12 foot tall ceilings, massive windows, an open layout, and fa ...
From $621 per night (USD)VRBO
- From $370 per night (USD)
VRBO
McCormick Place 2b\/2b family unit with optional parking for up to 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • Amazing City view • ...
From $370 per night (USD)VRBO
- From $345 per night (USD)
VRBO
McCormick Place 2b\/2b family unit with optional parking for up to 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • City Skyline view • ...
From $345 per night (USD)VRBO
- From $365 per night (USD)
VRBO
Warm and Cheerful 3 Bedroom Winnetka Townhouse
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in comfort in the ChicagoLand north shore in a 3 bedroom, 1.5 bath, 2-car garage townhome only blocks from Metra ra ...
From $365 per night (USD)VRBO
- From $360 per night (USD)
VRBO
McCormick Place 2b\/2b family unit with optional parking for up to 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
• Please MESSAGE US for SPECIAL RATES • Steps away from McCormick Place • Michigan Avenue location • City Skyline view • ...
From $360 per night (USD)VRBO
- From $423 per night (USD)
VRBO
Extended Stay Summit FHS Rental
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Summary: 2340 SF renovated home is only 3 miles away from Midway airport, and approx. 16 min from downtown Chicago! Th ...
From $423 per night (USD)VRBO
- From $1242 per night (USD)
VRBO
858 - Floor 2: Comes with Private Patio and 2 Apartments!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
This listing contains the following: - You will have your own private floor and access to 2 individual Suites across th ...
From $1242 per night (USD)VRBO
- From $344 per night (USD)
VRBO
858 3N - BEAUTIFULLY remodeled flat DOWNTOWN - West Elm Furniture!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
BRAND NEW REMODEL BUILT SPECIFICALLY FOR VRBO! The entire property is designed by a famous Chicago Designer using stric ...
From $344 per night (USD)VRBO
- From $86 per night (USD)
VRBO
Lovely Loop 1BR w\/ Gym, Roof Deck, near Millennium Park, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Discover the best of Chicago, with this one-bedroom The Loop apartment with views over the city. It’ll be easy to simpl ...
From $86 per night (USD)VRBO
- From $1194 per night (USD)
VRBO
858 - Floor 3: Includes a Private Rooftop Patio!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
The unit contains the following: - You will have your own private floor and access to 2 individual Suites across the ha ...
From $1194 per night (USD)VRBO
- From $576 per night (USD)
VRBO
858 2S - Downtown Penthouse with Private Rooftop!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
The entire property is designed by a famous Chicago Designer using strictly West Elm brand furniture. You do not want to ...
From $576 per night (USD)VRBO
- From $3338 per night (USD)
VRBO
The Orleans - Entire Building - With Rooftop Deck!
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 16
Summary: This property can be rented out and you would have access to the entire building which consists of 4 individual ...
From $3338 per night (USD)VRBO
- From $354 per night (USD)
VRBO
McCormick Place Skyline view 2b\/2b unit with optional parking for up to 6 guests
- 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 $354 per night (USD)VRBO
- From $258 per night (USD)
VRBO
Mid Century Elegance in Evanston Vintage Apartment.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Evanston and a short walk from Evanston's Central Street Business District, and scenic Lake Michigan beaches, ...
From $258 per night (USD)VRBO
- From $318 per night (USD)
VRBO
Diversey #2 Lincoln Park-Short walk to Wrigley, Lincoln Park and The Beach!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 10
This place was FULLY remodeled for one purpose - to host guests like yourself! It is designed with you in mind! We don't ...
From $318 per night (USD)VRBO
- From $101 per night (USD)
VRBO
Stylish 2BR Condo - Steps from Eats, Bars & Shops!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Modern 2 Bedroom + 2 Bath Condo in the heart of Chicago's East Village! Tucked between Division St and Chicago Ave, this ...
From $101 per night (USD)VRBO
- From $192 per night (USD)
VRBO
BEST LOCATION!! LUX 2b\/2b Condo, 51st Floor AMAZING Views, Great Amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Luxury condo in a FANTASTIC location! Newly remodeled upscale condo located on the brink of River North/Gold Coast/Stree ...
From $192 per night (USD)VRBO
- From $200 per night (USD)
VRBO
Wrigleyville Home away from Home! 5 mins from downtown! steps from Lake!! Cozy!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully furnished Three Bedroom, Two Bath. Walking distance from the lakefront, and a short bus ride to Michigan Av ...
From $200 per night (USD)VRBO
- From $450 per night (USD)
VRBO
3 Kng, 1 Qn, 1 Full, 3air Bds | Private Basketball Court | FreePKG
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
Sitting on half-acre, 3,000 sqft custom Prairie-inspired Home with 4 bedrooms, 2.5 baths, open-floor concept kitchen, di ...
From $450 per night (USD)VRBO
- From $121 per night (USD)
VRBO
Airy West Loop 1BR w\/ Pool, Pet Spa, near Restaurant Row, by Blueground
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Show up and start living from day one in Chicago with this spacious one-bedroom Blueground apartment. You’ll love coming ...
From $121 per night (USD)VRBO