Holiday houses in Chicago Loop

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Popular amenities for Chicago Loop holiday rentals

Stay near Chicago Loop's top sights

Millennium Park1,243 locals recommend
Navy Pier933 locals recommend
Shedd Aquarium673 locals recommend
The Field Museum657 locals recommend
Willis Tower Skydeck348 locals recommend
Au Cheval620 locals recommend

Other great holiday rentals in Chicago Loop

Superhost
Home in West Lawn
4.95 out of 5 average rating, 37 reviews

Family Friendly Duplex/9 min from MDW/Free Parking

AshleyRating, 5 stars3 weeks ago
Johanna made us feel warm and welcome. All amenities are included and work well. Excellent shower. She was very responsive and attentive.
Guest favourite
Home in Elmhurst
4.86 out of 5 average rating, 22 reviews

Enamored in Elmhurst

YvonneRating, 5 stars2 weeks ago
This home is in a beautiful neighborhood. It was very clean and the decor was simple yet stunning. There was plenty of linen and the kitchen was stocked well enough to cook an entire meal Mark was very responsive and provided clear instructions for check in and out. I would stay here again
Guest favourite
Apartment in West Town
4.85 out of 5 average rating, 128 reviews

Condo with private terrace, free WIFI and parking

OlegRating, 5 stars1 month ago
We have traveled to Chicago with a party of 5 - 3 adults and 2 kids in February 2025. We stayed for 3 nights and really liked Mark's place. It is really bigger than it shows on the pictures, so it really accomodates 6-8 people easily. Host was responsive and provided helpful and timely instructions. Would stay again.
Guest favourite
Apartment in Albany Park
4.86 out of 5 average rating, 42 reviews

Elegant 4Bedroom with Free Parking in Albany Park

MatthewRating, 5 stars2 months ago
Wonderful stay as always, thank you so much!
Superhost
Apartment in Jefferson Park
4.65 out of 5 average rating, 23 reviews

City Gem: Stylish 3BR for Urban Explorers

AnnikaRating, 5 stars2 weeks ago
Peaceful, felt like home, very spacious and comfortable
Superhost
Condo in East Rogers Park
4.79 out of 5 average rating, 29 reviews

Spacious condo with open floor plan and fireplace

TatianaRating, 5 stars3 months 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.
Superhost
Home in Cicero
4.79 out of 5 average rating, 177 reviews

Spacious whole apt near shopping and city

AdedolapoRating, 5 stars1 week ago
Beautiful and excellent place host was very helpful
Top Guest favourite
Home in Lombard
5 out of 5 average rating, 24 reviews

Spacious Home in Chicago Suburbs

KimberlyRating, 5 stars3 weeks ago
Great place! It was easy to get in and out of. The host was very responsive! We would definitely stay again.

Quick stats about holiday rentals in Chicago Loop

  • Total rentals

    1.1K properties

  • Total number of reviews

    27K reviews

  • Family-friendly rentals

    290 properties are a good fit for families

  • Pet-friendly rentals

    610 properties allow pets

  • Rentals with a pool

    510 properties have a pool

  • Rentals with dedicated workspaces

    670 properties have a dedicated workspace

Destinations to explore

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