West Side Vacations from $612
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The Latest West Side vacation packages
Price found within the past 48 hours. Click for updated prices.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $1,088, price is now $612 per person
$612
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,992 reviews)
Our experience here was fantastic. We visited in August and the weather was superb. Everything was centralized. From shopping to dining and peace and quiet were abound. Just magnificent stay. The staff was friendly and informative. Thank you.
Reviewed on Sep 4, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,385, price is now $737 per person
$737
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,373 reviews)
My go to spot to stay in Chicago
Reviewed on Sep 7, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,396, price is now $807 per person
$807
per person
Nov 21 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,195 reviews)
We have stayed here a handful of times now and consistently have the best time. The staff is always friendly and helpful. The rooms are clean and comfortable. We love grabbing some cocktails and a snack at Fora and ending our night on the rooftop. We also have been to Sushi By Bou a handful of times and have the most amazing experience. The location is beautiful, safe and convenient. Walkable to all the Chicago things we love to do. I recommend The Emily to everyone I know traveling to Chicago and we can’t wait for our next visit!
Reviewed on Sep 7, 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,975, price is now $1,170 per person
$1,170
per person
Nov 24 - Nov 29
found 24 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,001 reviews)
Excellent service with great top notch amenities and a room that has everything you can need away from home. Highly recommend!
Reviewed on Aug 31, 2025
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 Milwaukee Avenue 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.
Discover the most popular places to visit in West Side
United Center
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its fascinating museums.
University of Illinois Chicago
Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed art scene in this vibrant area.
Humboldt Park
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 acclaimed theater scene and fascinating museums in this vibrant area.
What to do in West Side
Wendella's 90-min Chicago River Architecture Tour
$45
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
West Side Hotel Deals
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
$190 nightly
The price is $223 total per night from Sep 28 to Sep 29
$223 total
Sep 28 - Sep 29
Total with taxes and fees
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street, Chicago, IL
Fully refundable
$179 nightly
The price is $210 total per night from Oct 5 to Oct 6
$210 total
Oct 5 - Oct 6
Total with taxes and fees
Hyatt Place Chicago Medical/University District
1835 W Harrison Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$206 nightly
The price is $242 total per night from Sep 14 to Sep 15
$242 total
Sep 14 - Sep 15
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.
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- Chicago Vacations
- Our Lady of Sorrows Basilica
- Anna and Frederick Douglass Park
- Visit East Garfield Park
- Garfield Park
- Garfield Park Conservatory
- United Center
- Visit United Center
- St. Basil Greek Orthodox Church
- Ukrainian Institute Of Modern Art
- St Nicholas Ukrainian Catholic Cathedral
- Mexican Fine Arts Center Museum
- Grace Abbott Homes Vacations
- National Museum of Puerto Rican Arts & Culture
- Visit Downtown Chicago
- University of Illinois Chicago
- Holy Trinity Russian Orthodox Cathedral
- Visit Ukrainian Village
- Credit Union 1 Arena
- Visit North Lawndale
- Monique Meloche Gallery
- Visit Grace Abbott Homes
- West Town Vacations
- Visit Humboldt Park
- Visit Little Village
- Wood Street Gallery
- Visit Lower West Side
- Mary Bartelme Park
- Car rentals near Chicago
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- Car rentals near United Center
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
