Northwest Side

Travel Guide

A curved pathway with a metal fence, flowering trees, and a street lamp.

The Chicago Theatre with a prominent marquee displaying movie titles.

A city skyline with several high-rise buildings, including a prominent glass skyscraper and a building with a spire.

Visit Northwest Side

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

€118

8 Sept - 9 Sept

includes taxes & fees

Stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, 2 bars/lounges and breakfast (surcharge). Our guests praise the helpful staff and the clean ...

8/10 Very good! (10,264 reviews)

"The shower didn't work very well."

Reviewed on 19 Aug 2026

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

€147

30 Aug - 31 Aug

includes taxes & fees

Stay at this business-friendly hotel in Chicago. Enjoy free Wi-Fi, a 24-hour fitness centre and valet parking (surcharge). Our guests praise the helpful staff ...

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

Stay at this aparthotel in Chicago. Enjoy free Wi-Fi, a fitness centre and parking (surcharge). Our guests praise the helpful staff in their reviews. Popular ...

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

Chicago IL

Stay at this family-friendly apartment in Chicago. Enjoy free breakfast, free Wi-Fi and a garden. Popular attractions Rosemont Theatre and Fashion Outlets of ...

10/10 Exceptional! (134 reviews)

"Jamie was wonderful from the get/go. Great communication, made sure we had a close parking spot to unload, gave us the grand tour and was extremely personable. She helped me through an incredible snafu I got my self into as well. I could not have gotten through it without her! Loved sitting on her ..."

Reviewed on 14 Aug 2026

Sleeps 18 • 8BR • Game Room • Gym • Theater

Chicago IL

Stay at this holiday home in Chicago. Enjoy a pool table, an in-room coffee maker and air conditioning. Popular attractions Wrigley Field and Rosemont Theatre ...

10/10 Exceptional! (6 reviews)

"Location was perfect. Really enjoyed Portage Park. Our large group fit comfortably."

Reviewed on 17 Aug 2026

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL

Stay at this aparthotel in Chicago. Enjoy free Wi-Fi, a fitness centre and parking (surcharge). Our guests praise the helpful staff in their reviews. Popular ...

See all properties in Northwest Side

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Northwest Side attractions

Portage Park

After visiting Portage Park, make a plan to see the other sights and activities in Chicago. Amble around this vibrant area's lakeside and enjoy its top-notch restaurants.

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