Stays with air conditioning in Chicago, IL
Stays with air conditioning in Chicago, IL, from $75 a night. Book direct on each manager's site, no OTA fee.
Find stays in Chicago, IL
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Stays, best documented first
4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
From $181 a night
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Premium 4 King Apartment w/ City Views
Apartment · 4 bed · 3 bath · sleeps 10
Chicago, IL
From $699 a night
- air conditioning
- bbq grill
- bed linens
- cable tv
Exact location
Book direct on Envitae
West Loop Condo Walk 2 Restaurants
Condo · 2 bed · 1 bath · sleeps 6
Chicago, IL
From $99 a night
- internet
- wireless
- air conditioning
- kitchen
Exact location
Book direct on Angie's Stays
Edgewater Apt with Free Parking, Gym, City Living
Apartment · 2 bed · 2 bath · sleeps 4
Chicago, IL
From $175 a night
- air conditioning
- baking sheet
- bed linens
- blender
Exact location
Book direct on CielStay
Bright 4BR Apartment Near Lincoln Park Zoo
Apartment · 4 bed · 3 bath · sleeps 10
Chicago, IL
From $193 a night
- air conditioning
- bbq grill
- bed linens
- blender
Exact location
Book direct on CielStay
Wrightwood Place | Lincoln Park 4BR Elegant Apartment
House · 4 bed · 3 bath · sleeps 12
Chicago, IL
From $367 a night
- body soap
- cleaning products
- conditioner
- hot water
Exact location
Book direct on Luxury Furnished Vacation Rentals & Property Management
Douglass Atelier | 3BR Home & Private Garden
House · 3 bed · 2 bath · sleeps 10
Chicago, IL
From $499 a night
- conditioner
- hair dryer
- bed linens
- dryer
Exact location
Book direct on Luxury Furnished Vacation Rentals & Property Management
Hotel Motel 6 Chicago, Il - Halsted Chicago
Hotel
Chicago, IL
From $75 a night
- 24-hour reception
- air conditioning
- pets allowed
City-level location
Book direct on Chicago hotels & apartments, all accommodations in Chicago
The Northside Nest
House · 2 bed · 1 bath · sleeps 6
Chicago, IL
No nightly rate published
- air conditioning
- central heating
- baking sheet
- coffee maker
Exact location
Book direct on The Boutique Home Group
1BR City Loft With Modern Glass Views
House · 1 bed · 1 bath · sleeps 4
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
2BR City Loft Sweeping Glass Views
House · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
2BR City Suite w/ Amazing Glass Views
House · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
2BR Designer Suite in City Center w/ Skyline Views
Apartment · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- air conditioning
- bathtub
- bed linens
- cable tv
Exact location
Book direct on Envitae
2BR/2BA Luxury Glass Apartment | Amazing Views
House · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- kitchen
- wifi
- dedicated workspace
- pets allowed
Exact location
Book direct on Envitae
3BR Apartment Near Clybourn Corridor & Old Town
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
3BR Luxury Suite w/Gym and Balcony
House · 3 bed · 2.5 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
4BR City Retreat, Great for Business & Family
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Bright 3BR Stylish Apartment Near North Ave Shops
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Bright 4BR Apartment Near Lincoln Park Zoo
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Bronzeville Gem: Balcony, Gym & Rooftop Deck
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Chic 4-Bedroom with Skyline Views, Firepit and Gym
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Cozy Studio Suite, Steps from River North & Shops
House · 0 bed · 1 bath · sleeps 4
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
ENVITAE Hotel / 4BR Luxury Modern Apartments
Apartment · 8 bed · 6 bath · sleeps 10
Chicago, IL
No nightly rate published
- air conditioning
- bbq grill
- bed linens
- carbon monoxide detector
Exact location
Book direct on Envitae
ENVITAE Hotel / 4BR Luxury Modern Apartments
Apartment · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- air conditioning
- bbq grill
- bed linens
- carbon monoxide detector
Exact location
Book direct on Envitae
Envitae Hotel, 4BR Modern Sleek Apartment
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Freshly Minted 2BR - Elegance & Comfort in Central Chicago
House · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Glass Views, 2 King Bed Perfect City Escape
House · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Luxury Apartment w/City Views, Downtown Location
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Modern & Bright Chicago City Escape
House · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Modern 1 King City Escape
House · 1 bed · 1 bath · sleeps 4
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Modern 2BR Retreat Near Old Town & Lincoln Park
House · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Modern 3BR City Retreat - Near Old Town
House · 3 bed · 2 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
New 4 King Bed / Family Ready Apartment
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
New, Modern 1 King City Escape
House · 1 bed · 1 bath · sleeps 4
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
New, Sleek 2BR - Perfect Blend of Comfort & Style in Chicago
House · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Premium Urban 4BR - Perfect Mix of Comfort & Location
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Sophisticated 4BR Suite - Walk to Shops, Dining & Transit
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
South Loop · 3 Kings · Steps from McCormick Place
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Spacious 3BR · Bronzeville/South Loop · Sleeps 8
House · 3 bed · 2 bath · sleeps 8
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Spacious 4BR Central Apartment w/ Skyline Views
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Spacious 4BR Near Fulton Market & Riverwalk
House · 4 bed · 3 bath · sleeps 10
Chicago, IL
No nightly rate published
- city skyline view
- kitchen
- wifi
- dedicated workspace
Exact location
Book direct on Envitae
Arts & Crafts Gem + Balcony | Food, Music, Shops
House · 3 bed · 1 bath · sleeps 6
Chicago, IL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- dryer
Exact location
Book direct on Boutique Stay + Balcony
Artsy Chicago: 1 bd/1 bth - Fun Modern Space
House · 1 bed · 1 bath · sleeps 4
Chicago, IL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- dryer
Exact location
Book direct on Luxurious Furnished Homes & Cozy Retreats
Atrio 1601
Apartment · 2 bed · 1 bath · sleeps 4
Chicago, IL
No nightly rate published
- 4th floor
- air conditioning
- in-unit laundry
Exact location
Book direct on Landing
Chicago Chic: 2 BR - 1 BA & Garage
House · 2 bed · 1 bath · sleeps 7
Chicago, IL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- dryer
Exact location
Book direct on Luxurious Furnished Homes & Cozy Retreats
City Center Oasis: 3BR/2BA✔︎ Patio✔︎ Parking(2x) ✔︎
Condo · 3 bed · 2 bath · sleeps 10
Chicago, IL
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- hair dryer
Exact location
Book direct on CielStay
Inside Info Fremont 309
Apartment · 0 bed · 1 bath · sleeps 2
Chicago, IL
No nightly rate published
- 3rd floor
- air conditioning
- in-unit laundry
- smart lock
Exact location
Book direct on Landing
Inside Info Fremont 310
Apartment · 0 bed · 1 bath · sleeps 2
Chicago, IL
No nightly rate published
- 3rd floor
- air conditioning
- in-unit laundry
- smart lock
Exact location
Book direct on Landing
Inside Info Fremont 409
Apartment · 0 bed · 1 bath · sleeps 2
Chicago, IL
No nightly rate published
- 4th floor
- air conditioning
- in-unit laundry
- smart lock
Exact location
Book direct on Landing
Inside Info Fremont 411
Apartment · 0 bed · 1 bath · sleeps 2
Chicago, IL
No nightly rate published
- 4th floor
- air conditioning
- in-unit laundry
- smart lock
Exact location
Book direct on Landing
Maison Blanc Noir
House · 5 bed · 3.5 bath · sleeps 15
Chicago, IL
No nightly rate published
- air conditioning
- airport transfer
- free wi-fi
- laundry
City-level location
Book direct on Wieser Host
Runway Retreat: 3 Levels, 3Bdrm, 1.5BA
House · 3 bed · 1.5 bath · sleeps 6
Chicago, IL
No nightly rate published
- air conditioning
- dishes and silverware
- dryer
- tv
Exact location
Book direct on Luxurious Furnished Homes & Cozy Retreats
Skylights, King Bed, 2 bedrooms
Apartment · 2 bed · 1 bath · sleeps 6
Chicago, IL
No nightly rate published
- air conditioning
- dishes and silverware
- hair dryer
- dedicated workspace
Exact location
Book direct on Windy City BNB
Spacious 3-Bedroom Ukrainian Village Home
House · 3 bed · 3 bath · sleeps 8
Chicago, IL
No nightly rate published
- air conditioning
- washer and dryer
- free wifi
- kitchen
City-level location
Book direct on Spacious 3-Bedroom Ukrainian Village Home with Private Deck
Stunning Designer Duplex in Fulton Market
Loft · 3 bed · 2.5 bath · sleeps 8
Chicago, IL
No nightly rate published
- air conditioning
- dishes and silverware
- hair dryer
- dedicated workspace
Exact location
Book direct on Updated Designer Duplex In Fulton Market W/parking
Stylish & Artsy 2BR 2BA | Wi-Fi | West Loop|
House · 2 bed · 2 bath · sleeps 6
Chicago, IL
No nightly rate published
- air conditioning
- dishes and silverware
- hair dryer
- tv
Exact location
Book direct on Seven Properties
The Aria®
Condo · 2 bed · 1 bath · sleeps 3
Chicago, IL
No nightly rate published
- air conditioning
- heating
- wifi
- iron
Exact location
Book direct on World Class®
The Astoria Highrise
House · 2 bed · 1 bath · sleeps 3
Chicago, IL
No nightly rate published
- air conditioning
- heating
- wifi
- washer
Exact location
Book direct on World Class®
The Atlas Highrise
House · 3 bed · 1 bath · sleeps 5
Chicago, IL
No nightly rate published
- premium appliances
- high speed wi-fi
- city views
- walk in closet
Exact location
Book direct on World Class®
The Celine Highrise
House · 2 bed · 1 bath · sleeps 3
Chicago, IL
No nightly rate published
- air conditioning
- heating
- wifi
- washer
Exact location
Book direct on World Class®
These are the cheapest; there are more. Narrow by facet above, or ask an agent through https://otaless.com/mcp.
How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-30 09:01 UTC. Prices and facts are whatever the manager published on their own site.