Holiday rentals in Chicago Loop

Find and book unique accommodation on Airbnb

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Popular amenities for Chicago Loop holiday rentals

Stay near Chicago Loop's top sights

Millennium Park1,243 locals recommend
Grant Park332 locals recommend
Shedd Aquarium673 locals recommend
Cloud Gate473 locals recommend
Willis Tower324 locals recommend
Skydeck Chicago124 locals recommend

Other great holiday rentals in Chicago Loop

Guest favourite

Flat in West Town

4.92 out of 5 average rating, 326 reviews

Bright, Modern Apartment in a Vintage Greystone

16–23 Jan

$194 SGD per night
Guest favourite

Flat in Wrigleyville

4.92 out of 5 average rating, 185 reviews

Taj Ma-small at Wrigley

10–17 Feb

$165 SGD per night
Guest favourite

Home in Bridgeport

4.95 out of 5 average rating, 120 reviews

Cozy & Modern Chic Full House in Trendy Bridgeport

9–16 Jan

$161 SGD per night
Guest favourite

Flat in Pilsen Historic District

4.85 out of 5 average rating, 233 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

15–22 Aug

$103 SGD per night
Guest favourite

Home in Pilsen Historic District

4.96 out of 5 average rating, 316 reviews

Get Cozy at a Powder-Blue Residence in the Heart of Pilsen

28 Jan – 4 Feb

$191 SGD per night
Guest favourite

Guest suite in Lake View

4.95 out of 5 average rating, 175 reviews

1 mile from Wrigley Field

5–12 Sep

$206 SGD per night
Guest favourite

Apartment in Lincoln Park

4.95 out of 5 average rating, 437 reviews

Unique Lincoln Park Duplex Apt

26 Sep – 3 Oct

$251 SGD per night
Guest favourite

Flat in Portage Park

4.96 out of 5 average rating, 50 reviews

Comfy & Private Chicago Studio

22–29 Jan

$120 SGD per night

Quick stats about holiday rentals in Chicago Loop

  • Total rentals

    890 properties

  • Rentals with dedicated workspaces

    600 properties have a dedicated workspace

  • Rentals with a pool

    480 properties have a pool

  • Pet-friendly rentals

    460 properties allow pets

  • Family-friendly rentals

    270 properties are a good fit for families

  • Total number of reviews

    31K reviews

Destinations to explore

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