West Side Vacations from $441
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The Latest West Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago
Downtown Chicago
$607
per person
Dec 2 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (5,340 reviews)
Everyone was very helpful. Breakfast options were plentiful. Rooms were clean and well laid out. Great central location to Lucasfilm activities.
Reviewed on Oct 1, 2026
Kimpton Gray Hotel by IHG
Downtown Chicago
$466
per person
Nov 19 - Nov 22
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,007 reviews)
Stayed one night on a quick trip for a show. We are regular travelers to Chicago. The hotel is in a wonderful historic building, really interesting 2nd floor lobby and sitting area. The lounge was closed on Sunday's so we missed it but it looked very nice. The hotel lobby offered a 5-6pm happy hour with wine and beer. The room was very nice and good size for Chicago. Not brand new, but still in good condition and clean. The bed was comfortable, the room was quiet. Kimpton hotels are usually great and this one was up to standard.
Reviewed on Sep 30, 2026
Where to stay in West Side
Find the best West Side areas and neighborhoods for the activities you enjoy most. Learn more about West Side
West Loop
1 out of top 10 points of interest in this area
Consider a visit to The Old Post Office and take some time to enjoy the abundant dining options during your time in West Loop. If you want to see more of the city, jump on the metro at Racine Station or Ogilvie Transportation Center.
West Town
2 out of top 10 points of interest in this area
Noted for its live music and theaters, there's plenty to explore in West Town. Top attractions like The Salt Shed and Milwaukee Avenue are major draws, and you can hop on the metro at Division Station or Damen Station to see more of the city.
Near West Side
4 out of top 10 points of interest in this area
Live music, theaters, and shopping highlight some notable features of Near West Side. Make a stop by United Center or Credit Union 1 Arena while you're visiting, and jump aboard the metro at Polk Station (Pink Line) or Racine Station to get around town.
Wicker Park
Consider exploring the abundant dining options in Wicker Park. If sightseeing is on the list, Milwaukee Avenue is a top attraction. Hop on the metro at Damen Station or Division Station to see more of the area.
Humboldt Park
While Humboldt Park might not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Garfield Park Conservatory and National Museum of Puerto Rican Arts & Culture.
Stay near popular West Side attractions
United Center
8.8/10 (4,269 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed theater scene.
University of Illinois Chicago
8.4/10 (1,058 reviews)
Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the fascinating museums in this vibrant area.
Humboldt Park
7.0/10 (2 reviews)
Humboldt Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Experience the fascinating museums and acclaimed art scene in this vibrant area.
Photo by Nina Huang
Garfield Park
After visiting Garfield Park, make a plan to see the other sights and activities in Chicago. Discover the top-notch restaurants and acclaimed theater scene in this vibrant area.
Anna and Frederick Douglass Park
7.0/10 (12 reviews)
After visiting Anna and Frederick Douglass Park, make a plan to see the other sights and activities in Chicago. Experience the acclaimed theater scene and fascinating museums in this vibrant area.
The Salt Shed
You can get tickets for a performance at The Salt Shed during your stay in Chicago. Experience the live music and theater scene in this vibrant area.
Union Park
After visiting Union Park, make a plan to see the other sights and activities in Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
Credit Union 1 Arena
8.0/10 (5 reviews)
Catch an event at Credit Union 1 Arena during your trip to Chicago. Stroll along the riverfront or experience the entertainment choices in this vibrant area.
What to do in West Side
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
West Side Hotel Deals
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
$153 nightly
$182 total
Nov 1 - Nov 2
Total with taxes and fees
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
$145 nightly
$172 total
Nov 1 - Nov 2
Total with taxes and fees
LIVN - West Loop Chicago
555 West Jackson Boulevard Chicago IL
$304 nightly
$357 total
Oct 2 - Oct 3
Total with taxes and fees
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.
Find the Best West Side Vacation Packages
West Side Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
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