
West Side Vacations from $557
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The Latest West Side vacation packages
Price found within the past 48 hours. Click for updated prices.

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $842, price is now $557 per person
$557
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Really small room.
Outside windows need cleaned.
Nice staff
Reviewed on Jun 30, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,127, price is now $737 per person
$737
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Good breakfast with a thoughtful selection of food. The quality of the ingredients is high, the dining area is well-maintained, and the overall choice is better than average.
Reviewed on Jun 30, 2026

Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,123, price is now $749 per person
$749
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,128 reviews)
The Pendry is in the heart of everything downtown. The blue line in from the airport was about a 7 minute walk from the lake stop. Rooftop bar is a nice visit as well as the lobby bar. Great staff, good vibes.
Reviewed on Jun 29, 2026

Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,365, price is now $925 per person
$925
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (495 reviews)
Front desk people was very helpful Eric was amazing was on top of everything and helped with everything as well
Reviewed on Jun 26, 2026

Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
Price was $938, price is now $637 per person
$637
per person
Sep 3 - Sep 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,821 reviews)
Room service was terrible other than that I really liked the hotel
Reviewed on Jun 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.
Stay near popular West Side attractions
What to do in West Side

Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% 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
$170 nightly
The price is $202 total per night from Jul 1 to Jul 2
$202 total
Jul 1 - Jul 2
Total with taxes and fees
9/10 Wonderful! (2,316 reviews)
"clean room staff was excellent!!!"
Reviewed on Jun 30, 2026

Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
$159 nightly
The price is $190 total per night from Jul 5 to Jul 6
$190 total
Jul 5 - Jul 6
Total with taxes and fees
8.8/10 Excellent! (1,044 reviews)
"Stay was amazing, staff were polite and helpful. Hotel parking is very limited, available parking in the area was good but definitely recommended getting SpotHero parking app definitely a lifesaver. The room I was staying in was great but the bathroom as a bit cramped and has water damage on the ..."
Reviewed on Jun 30, 2026

The Emily Hotel
311 North Morgan Street Chicago IL
$320 nightly
The price is $380 total per night from Jul 26 to Jul 27
$380 total
Jul 26 - Jul 27
Total with taxes and fees
9.2/10 Wonderful! (1,323 reviews)
"Clean rooms, great location, helpful staff"
Reviewed on Jun 29, 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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




























