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Vacation rentals in Chicago Loop

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Popular amenities for Chicago Loop vacation rentals

Stay near Chicago Loop's top sights

Millennium Park1,242 locals recommend
Navy Pier933 locals recommend
University of Illinois at Chicago27 locals recommend
Shedd Aquarium673 locals recommend
Northerly Island45 locals recommend
The Field Museum657 locals recommend

Other great vacation rentals in Chicago Loop

Guest favorite
Home in West Lawn
4.94 out of 5 average rating, 34 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

NoelleRating, 5 stars1 week ago
Loved our stay in Chicago! Johanna was a WONDERFUL host!! Very helpful and very clear instructions for check in and out. When I needed to get ahold of her it was super easy to connect with her. House is adorable and very home like feeling :) would definitely recommend staying here!
Guest favorite
The open living area is highlighted by a neutral color palette and modern furnishings. A coffee table sits in the center, and a flat-screen TV is mounted on the wall. Natural light is filtered through large windows, enhancing the spacious feel of the room.
Home in Elmhurst
4.83 out of 5 average rating, 18 reviews

Enamored in Elmhurst

MarieRating, 5 stars3 weeks ago
So happy this was available for a last minute trip to Elmhurst — very comfortable and clean! Easy to get around the area and Mark was easy to communicate with and responsive!
Guest favorite
A private rooftop space features a green surface and a set of outdoor furniture, including a round table surrounded by several metal chairs. The backdrop is dominated by a historic red-brick building with distinctive domes and architectural details.
Apartment in West Town
4.85 out of 5 average rating, 126 reviews

Condo with private terrace, free WIFI and parking

AaronRating, 5 stars6 months ago
Great place, very clear and easy instructions, close to everything you need in the city, made a mistake with booking and they made it extremely easy and very flexible to stay an extra night.
Guest favorite
A living room features two yellow chairs positioned beside a small table. A large painting of a pelican adorns one wall, while large windows allow natural light to fill the space. A tan area rug covers the dark wooden floor, enhancing the room's inviting atmosphere.
Home in Chicago
4.92 out of 5 average rating, 12 reviews

A home away from home.

NicoleRating, 5 stars5 months ago
Me my freinds and family enjoyed our stay. The host was very quick to respond to any concerns. The home was clean and spacious. The decor was nice to take pictures. I liked that it had a bathroom downstairs for easy assess. We will come back when we visit Chicago again. Thanks you guy you were awesome.
Guest favorite
A light-filled living area showcases two comfortable armchairs and a cozy sofa arranged around a central coffee table. A sleek stone fireplace serves as a focal point, while built-in shelves display decorative items and plants, contributing to a welcoming ambiance.
Apartment in Albany Park
4.95 out of 5 average rating, 39 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars1 month ago
Thank you for letting us stay in your beautiful home. Everything was exactly as described! Will definitely stay again
Superhost
Apartment in Jefferson Park
4.81 out of 5 average rating, 16 reviews

City Gem: Stylish 3BR for Urban Explorers

MaríaRating, 5 stars2 months ago
Excellent lodging and host, I would come back!
Superhost
An open living and dining area is shown, featuring a flat-screen TV mounted on a light wood unit. Comfortable seating includes a gray sofa, teal chairs, and a pink armchair. A wooden dining table is set for six. Decorative elements include wall art and a wall clock.
Home in Logan Square
4.86 out of 5 average rating, 90 reviews

California Cottage/4br prime location Logan Square

JoelRating, 5 stars1 month ago
This truly was an excellent deal for all of the space and the location. The beds were comfy. The layout has great communal space. Very clean and well maintained. We would definitely stay here again.
Superhost
An open living area features a comfortable sofa positioned around a stone fireplace, with a dining table set for six nearby. Natural light fills the room through multiple windows, and a television is mounted on the wall, offering entertainment options.
Condo in East Rogers Park
4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars1 month ago
This place was spacious and perfect for our family (two kids and a baby), with plenty of room for everyone to spread out. The hosts were fantastic! They encountered an issue with the fridge not working just before our arrival but handled it professionally, providing excellent support until it was fixed. We really appreciated their responsiveness and care. We highly recommend this space for families and large groups. One small suggestion: if you’re a light sleeper or have kids, consider bringing a noise machine, as some sound from the upstairs neighbors can be heard. However, this wasn’t a problem for us and is to be expected when staying in a condo.

Quick stats about vacation rentals in Chicago Loop

  • Total rentals

    1K properties

  • Total number of reviews

    28K reviews

  • Family-friendly rentals

    290 properties are a good fit for families

  • Pet-friendly rentals

    580 properties allow pets

  • Rentals with a pool

    450 properties have a pool

  • Rentals with dedicated workspaces

    710 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Illinois
  4. Cook County
  5. Chicago
  6. Chicago Loop