West Side Vacations from $240
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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 $409, price is now $240 per person
$240
per person
Feb 3 - Feb 8
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8/10 Very Good! (478 reviews)
We had to switch rooms due to not having hot water but the staff was very good and switched us with no issues
Reviewed on Dec 20, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $760, price is now $418 per person
$418
per person
Jan 23 - Jan 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!
Reviewed on Dec 14, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $595, price is now $329 per person
$329
per person
Feb 25 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,790 reviews)
Great stay, breakfast was plentiful. Decorations around the lobby made it feel very festive.
Reviewed on Dec 22, 2025
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $659, price is now $383 per person
$383
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,264 reviews)
The room was awesome! The neighborhood was awesome but the real champs were the staff! Demetrius took extra special care of us for our special evening and it made it incredible!
We will absolutely be back anytime we’re in the city and if you want a clean, enjoyable, tentative stay this is the place to go to!
Reviewed on Dec 21, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $970, price is now $569 per person
$569
per person
Feb 26 - Mar 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,773 reviews)
Loved it here and would stay again! Everything was perfect!
Reviewed on Dec 21, 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
4.5/5(701 reviews)
Catch an event at United Center during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
University of Illinois Chicago
4/5(832 reviews)
Enjoy the collegiate vibe at University of Illinois Chicago during your stay in Chicago. Stroll along the riverfront or experience the entertainment choices 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
Chicago Bulls Basketball Game at United Center
$80
per adult
80% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
West Side Hotel Deals
Crowne Plaza Chicago West Loop by IHG
25 South Halsted Street Chicago IL
Fully refundableReserve now, pay when you stay
$91 nightly
The price is $107 total per night from Dec 28 to Dec 29
$107 total
Dec 28 - Dec 29
Total with taxes and fees
8.8/10 Excellent! (1,786 reviews)
Yes, everything was perfect.
Reviewed on Dec 21, 2025
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundable
$107 nightly
The price is $126 total per night from Dec 25 to Dec 26
$126 total
Dec 25 - Dec 26
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
Excellent
Reviewed on Dec 21, 2025
Hyatt House Chicago Medical/University District
1835 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Dec 29 to Dec 30
$109 total
Dec 29 - Dec 30
Total with taxes and fees
9/10 Wonderful! (1,269 reviews)
Nice room
Reviewed on Dec 20, 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.
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
- Our Lady of Sorrows Basilica
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- Visit East Garfield Park
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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.
