Near West Side Vacations from $238
Book a Hotel + Flight or Car together to unlock savings
Your Near West Side Vacation
Organizing your next getaway just got a whole lot easier with a vacation package to Near West Side. Enjoy all this neighborhood has to offer while making nice memories you won't forget. When it's time to sightsee, you'll find lots of top attractions nearby including University of Illinois Chicago, United Center and Anna and Frederick Douglass Park. Visit one, two or more during your trip to Near West Side. Stop daydreaming and start doing. When you're ready to book your dream vacation to Near West Side, Expedia will help get you there.
The Latest Near West Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hilton Grand Vacations Club Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $468, price is now $238 per person
$238
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (291 reviews)
Food price was high but everything was fine
Reviewed on Oct 4, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $531, price is now $280 per person
$280
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Location is excellent, roof top bonus and breakfast double plus.
Reviewed on Oct 8, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $620, price is now $333 per person
$333
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
The bed was extremly comfortable Staff was very attentive. Highly recommend
Reviewed on Oct 7, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $1,509, price is now $820 per person
$820
per person
Nov 24 - Nov 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
I stayed at the Trump International Washington DC, and this one pales in comparison to be honest. The staff was friendly/excellent, but the hotel itself was pretty standard. I expected the same level as the old Washington DC hotel. The shower was plugged up and drained as slow as frozen molasses.
Reviewed on Oct 6, 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,402, price is now $1,381 per person
$1,381
per person
Nov 21 - Nov 27
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
Awesome room amazing tub even better service
Reviewed on Oct 2, 2025
Where to stay in Near West Side
Find the best Near West Side areas and neighborhoods for the activities you enjoy most. Learn more about Near West Side
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Near West Side Hotel Deals
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street, Chicago, IL
Fully refundableReserve now, pay when you stay
$131 nightly
The price is $154 total per night from Nov 2 to Nov 3
$154 total
Nov 2 - Nov 3
Total with taxes and fees
8.8/10 Excellent! (1,576 reviews)
"I was glad but surprised that my package included parking. We never left, but upon check out, the gate wouldn’t go up, and the machine told us to pay. I went to tell the front desk, and the worker came out and made the gate go up for us!"
Reviewed on Oct 6, 2025
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street, Chicago, IL
Fully refundable
$157 nightly
The price is $185 total per night from Nov 6 to Nov 7
$185 total
Nov 6 - Nov 7
Total with taxes and fees
8.2/10 Very Good! (1,006 reviews)
"Great location that offers easy walking access to attractions and dining options. Uber is convenient for longer explorations. Clean and quiet rooms. A little threadworn, could use an update. Overall, a great value for a safe and comfortable stay in Chicago."
Reviewed on Oct 7, 2025
Level Chicago Fulton Market
354 North Union Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$219 nightly
The price is $257 total per night from Nov 6 to Nov 7
$257 total
Nov 6 - Nov 7
Total with taxes and fees
9/10 Wonderful! (314 reviews)
"Great place will return"
Reviewed on Oct 2, 2025
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.
Discover the most popular places to visit in Near 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 acclaimed theater scene.
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 fascinating museums in this vibrant area.
Mary Bartelme Park
After visiting Mary Bartelme Park, make a plan to see the other sights and activities in Chicago. Experience the acclaimed art scene and fascinating museums in this vibrant area.
Things to do
Skydeck - Willis Tower Admission
$44
per adult
100% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
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- Chicago Vacations
- Visit Downtown Chicago
- University of Illinois Chicago
- Credit Union 1 Arena
- Jane Addams' Hull-House Museum
- Mary Bartelme Park
- Willis Tower
- West Loop Vacations
- Maxwell Street Market
- Visit Greektown
- St. Basil Greek Orthodox Church
- Packer Schopf Gallery
- Visit Chicago
- 311 S Wacker Dr
- Skydeck Ledge
- Civic Opera House
- Chicago Board of Trade Building
- Grace Abbott Homes Vacations
- Where to stay in Chicago
- Visit West Loop
- United Center
- Car rentals near Chicago
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- Car rentals near University of Illinois Chicago
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- Hertz Rental Cars in West Loop
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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.