West Side Vacations from $373
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The Latest West Side vacation packages
Price found within the past 48 hours. Click for updated prices.
Illinois Beach Hotel
Save 100% on your flight
Price was $533, price is now $373 per person
$373
per person
Jul 14 - Jul 18
found 1 hour ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8/10 Very Good! (516 reviews)
Rented a beach view room. But they didn’t have a clean one available, had to pay more to upgrade to a suite.
Reviewed on May 8, 2026
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,096, price is now $719 per person
$719
per person
Jul 17 - Jul 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (468 reviews)
Love the amenities. Great location too
Reviewed on May 3, 2026
La Banque Hotel
Save 100% on your flight
Price was $686, price is now $454 per person
$454
per person
Aug 1 - Aug 4
found 2 days ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9.4/10 Exceptional! (484 reviews)
Easy and secure parking. Onsite gym. Restaurants located in lobby and surrounding areas, also has continental breakfast. Room was very clean
Reviewed on May 8, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,306, price is now $890 per person
$890
per person
Jun 11 - Jun 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (3,991 reviews)
Clean room and close to vicinity.
Reviewed on May 9, 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 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
4.5/5(718 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
4/5(838 reviews)
Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the acclaimed theater scene in this vibrant area.
Humboldt Park
3.5/5(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 acclaimed art scene and fascinating museums in this vibrant area.
What to do in West Side
Skydeck - Willis Tower Admission
$44
per adult
96% of travellers recommend
West Side Hotel Deals
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundable
$135 nightly
The price is $161 total per night from May 25 to May 26
$161 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (2,161 reviews)
👎
Reviewed on May 9, 2026
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
$132 nightly
The price is $157 total per night from May 25 to May 26
$157 total
May 25 - May 26
Total with taxes and fees
8.6/10 Excellent! (1,014 reviews)
..
Reviewed on May 9, 2026
The Hoxton Chicago
200 N Green Street Chicago IL
$228 nightly
The price is $272 total per night from May 10 to May 11
$272 total
May 10 - May 11
Total with taxes and fees
9.2/10 Wonderful! (1,012 reviews)
Comfortable, convenient location
Reviewed on May 3, 2026
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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- Chicago Vacations
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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.
