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Vacation rentals in Downtown Chicago

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Top-rated holiday rentals in Downtown Chicago

Guests agree: these stays are highly rated for location, cleanliness, and more.

Restoring Chicago Speakeasy from 1920's Room 1A
SUPERHOST
Private room · 2 guests · 2 beds · 1 private bath

Restoring Chicago Speakeasy from 1920's Room 1ANote : Check in is at noon but you can come as early as you need pick up the keys and drop off your things. Welcome to an Authentic Chicago Speakeasy from the 1920s. Your room is numbered 1A and your keys will be marked 1A. We are currently restoring this original Speakeasy from the 1920s to its former glory. There is an additional $50 fee per person for the third and fourth guests staying in the room. PLEASE NOTE:::: We are cleaning painting and doing light construction during the day here in the common areas. Please be advised. Please read the complete summary before you book. It is not fair for anyone to be given a bad review because someone didn't read the summary of what they were booking. Thank you for understanding this. Your bedroom is completely restored. and the main bath is totally adequate for your needs. Some work will be going on during the daytime in the common areas. No work is done after 6:00 in the evening. Feel free to walk throughout the two floors and observe the restoration process. I am an artist for over 40 years and will be opening M gallery on the second floor. It will be an art gallery and event space hosting art exhibits and concerts. We are loving this grand space and the process of restoring it. Come join us. michaelmccafrey.com

Great location. Free parking.
SUPERHOST
Entire rental unit · 2 guests · 1 bed · 1 bath

Great location. Free parking.Great location in Chicago's Wicker Park/Bucktown community. Fully furnished living room, bedroom with queen bed and bathroom. Internet, central heating/ac, small refrigerator, microwave, cable TV, dvd/Blu-ray, coffee maker. Small safe. Private free parking. One block from blue line (Division). From O’Hare via train – 35 min. 10 min to the city via blue line.

SHARED Artist Loft . Very Unique
SUPERHOST
Private room · 3 guests · 1 bed · 1 private bath

SHARED Artist Loft . Very UniqueNote: Check-in is at noon but you can come earlier pick up the keys and drop off your bags. NOTE: If the date your looking for is not available i have another beautiful room listed as, Artist Loft own private room. Look for it. Thank you. A BRIGHT airy loft bedroom with curtains for privacy, A beautiful room to wake up in. Flowered outdoor deck in the middle of famous River North Chicago is a wonderful start to enjoying everything this great city has to offer. This neighborhood is rocking on weekends. If a super light sleeper this room is not for you on weekends check my other listing. There is a $50 fee per person for the third and fourth person staying in the room.

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Popular amenities for Downtown Chicago holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Downtown Chicago

PLUS
  1. Entire rental unit
  2. Chicago
Redesigned Lower Level Studio in Historic Building
$180 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great Location Studio II
$113 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
420 friendly 3BR/2BA heaven with optional parking
$318 AUD per night
SUPERHOST
  1. Private room
  2. Chicago
In the heart of Pilsen, Self Check In
$60 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Charming apartment in Old Town
$159 AUD per night
  1. Entire rental unit
  2. Chicago
Beautifully Renovated, Walking distance to Lake!
$124 AUD per night
PLUS
  1. Entire guesthouse
  2. Chicago
Polk Street Coach House Apartment, Little Italy/Medical Dist
$165 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Beautiful and spacious West Loop apartment.
$283 AUD per night
PLUS
  1. Entire rental unit
  2. Chicago
Trendy West Loop Brownstone with Front Garden
$129 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great Location!!-12
$122 AUD per night
SUPERHOST
  1. Entire loft
  2. Chicago
Lakeview Loft-Vintage Chicago, Modern Amenities
$147 AUD per night
SUPERHOST
  1. Entire condominium (condo)
  2. Chicago
3 bedroom condo minutes from Downtown
$211 AUD per night

Top-rated things to do in Downtown Chicago

Unique activities hosted by local experts vetted for quality

  • Gangsters and Ghosts Tours
    One of the best ways to really acquaint yourself with the infamous city of Chicago is to do it from the streets, through a guided Chicago Gangster Tour or Ghost Tour, detailing the crimes, deals, and charisma that made the city what it is today. We offer a 2 for 1 deal, hosting historically-based guided tours of Chicago’s gangers AND ghost stories, right from the Chicago Loop Vice District. Other things to note Bring your camera!
    From Price:$38 / person
  • Explore Dazzling Architecture Interiors
    Take the architecture tour voted #1 by TripAdvisor users! We will be taking a leisurely 2-hour walk exploring some of the most beautiful and often overlooked buildings in downtown Chicago, both outside and inside, and learning about the most important and interesting parts of Chicago's architectural history. Visitors often don't know where to go, or even where they're allowed. This experience takes them inside places they'd never even consider, to show off more than 100 years of architecture as it developed here in the Windy City -- including stunning stained glass, atrium-like spaces, 19th century skyscrapers, and more! Great tour for photographers and travel buffs! Some things to note: Bring a camera -- this is an AWESOME way to practice your architecture photography! Also, dress for the weather, and if it's raining, bring an umbrella. Also, please note that if you provide a non-US phone number as your day-of contact number, we **CANNOT** call you if you're lost or late!
    From Price:$42 / person
  • Chicago's Underground Donut Tour
    On this tour, you'll join me as we explore the city and food culture through the medium of donuts. You'll learn about the history of Chicago, each donut location, how they fit into the larger food scene, as well as try some amazing donuts. We start from Doughnut Vault where we try some of the best donuts you've had in your life. Next we'll stop by Firecakes donuts to try a few of their seasonal flavors. Followed up with Stans Donuts near Michigan avenue and finally, we end at Do-Rite Donuts where they have both delicious donuts and fried chicken (if you want to get nuts at the end of the tour). We look forward to seeing you soon! Other things to note Let us know ahead of time if you have any dietary restrictions (gluten free, vegan, peanut allergy, etc.)
    From Price:$42 / person
  • MUST HAVE CHICAGO PHOTOS- OUTDOORS
    IF YOU DON´T SEE A TIME FRAME THAT WORKS FOR YOU PLEASE CONTACT ME AND WE CAN ARRANGE THAT We’ll start with a talk in Chicago Cultural Center by the bull and get to know each other. If it’s a small group during the experience, we will walk together around various locations but everybody has their own personal time with me while I photoshoot. Together we’ll discover the places and pictures that YOU NEED TO HAVE from Chicago , from the magical MILLENNIUM PARK, THE BEAN , CHICAGO THEATER AND RIVER WALK while I capture moments of you and/or any friends or your partner to take home. Feel free to tell me your ideas or preferences Other things to note THIS IS A SMALL GROUP EXPERIENCE AND EVERYBODY HAS THEIR OWN TIME (YOU CAN ALSO HAVE PRIVATE PHOTO SHOOTINGS IN CASE THAT YOU NEEED SOMETHING MORE PRIVATE) Please feel free to visit more of my work at www.carlacarrascoocampo.com also on IG at carrascoocampo
    From Price:$136 / person
  • All-Weather Architecture & History Trek
    I pack lots of sights, sounds and experiences on this tour so put on your walking shoes! We first meet in a sheltered spot to discuss the tour and begin our way trekking through Chicago. We'll use the expansive city sidewalks, plazas, parks and Riverwalk as well as part of the underground Pedway system that is known to only a percentage of Chicagoans (we have 5 miles of Pedway!). Learn about the history of The Windy City (as well as why we're REALLY called The Windy City) while digesting some of our city's most prominent sights. Using some of the Loop's buildings and sculptures, we'll get rare, unique views and traverse the city like a local. If you're curious about Prohibition-era gangster lore or our speakeasy past, we can cover that too. Be prepared for indoor and outdoor walking as our trek will take us outside, especially during warmer weather. Please let me know if you have any allergies or food sensitivities, as we’ll be stopping for an authentic Chicago snack that's been around for more than a century. Whether you're a local or this is your first visit, I promise to pack lots of interesting tidbits into our 2 hours together! COVID-19 UPDATE: We're spending more time outside as there is PLENTY to see & keeping the groups small so we can practice safe social distancing.
    From Price:$41 / person

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