
West Side Vacations from $717
Book a Hotel + Flight or Car together to unlock savings
Photo by throwingsofas
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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 $1,200, price is now $717 per person
$717
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,797 reviews)
Location was excellent. Rooms were a little smaller than I'd prefer but we got by.
Reviewed on Jun 29, 2026

Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,673, price is now $927 per person
$927
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,518 reviews)
Included breakfast was great. Very responsive. Our shower drain was clogged; they fixed it the evening we reported it.
Reviewed on Jun 29, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,105, price is now $1,280 per person
$1,280
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Clean room and staff was great.
Reviewed on Jun 28, 2026

Fairmont Chicago at Millennium Park
Downtown Chicago
Save 100% on your flight
Price was $1,162, price is now $750 per person
$750
per person
Sep 3 - Sep 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (2,222 reviews)
Great experience! Thanks!
Reviewed on Jun 29, 2026

Eurostars Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,261, price is now $828 per person
$828
per person
Aug 22 - Aug 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (3,668 reviews)
Amazing staff, safe location, and beautiful property! If and when I return to Chicago, I will be staying here!
Reviewed on Jun 29, 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! (2,314 reviews)
"The front desk staff were so sweet. I came to town for my birthday and they made it extra special! All of the staff were helpful, we felt so welcomed. The rooms were also pretty quiet, we couldn't hear anything in the rooms. The patio was also a nice touch."
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! (1,042 reviews)
"Front desk staff here is especially friendly and helpful. This is also so close to the main train station and also the clinton blue line subway which makes it a great spot!"
Reviewed on Jun 28, 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) |
More vacations you might like
Explore a world of travel with Expedia
- Grace Abbott Homes Vacations
- Grant Park
- Harold Washington Library Center
- Michigan Avenue
- Fourth Presbyterian Church
- Michigan Avenue Bridge
- The Loop Vacations
- Wrigley Field
- Maxwell Street Market
- Cadillac Palace Theatre
- Rookery
- Chicago Board of Trade Building
- University of Illinois Chicago
- Chicago City Hall
- Picasso Statue
- Daley Plaza
- Lincoln Park Conservatory
- Holy Name Cathedral
- Gorilla Tango Theatre
- Gen. John Logan Memorial
- Cibc Theatre
- Marshall Field Building
- The East Bank Club
- Monadnock Building
- House of Blues Chicago
- Cooking & Hospitality Institute of Chicago
- Ping Tom Memorial Park
- Humboldt Park
- Chicago Museum Campus Vacations
- Flat Iron Building
- American Police Center & Museum
- Water Tower Place
- Bally's Casino Chicago
- Navy Pier
- Auditorium Building and Theatre
- Driehaus Museum
- Jane Addams' Hull-House Museum
- Packer Schopf Gallery
- St Nicholas Ukrainian Catholic Cathedral
- Aon Center
- Marina City
- Wicker Park Vacations
- Chicago Vacations
- Richard J. Daley Center
- Wrigley Building
- Anna and Frederick Douglass Park
- 311 S Wacker Dr
- Chicago Loop Synagogue
- Our Lady of Sorrows Basilica
- Buckingham Fountain
- Chicago Place Mall
- 333 West Wacker Drive
- Merchandise Mart
- Millennium Park
- Downtown Chicago Vacations
- Film Row Cinema
- Roosevelt University
- Unity Temple
- River North Vacations
- Chicago History Museum
- Canalport Riverwalk Park
- St. John Cantius Church
- West Loop Vacations
- Goose Island Vacations
- Lincoln Park Zoo
- Cloud Gate
- International Museum of Surgical Science
- Crown Fountain
- Depaul University-Loop Campus
- North Avenue Beach
- Oak Street Beach
- Chicago Riverwalk
- Monique Meloche Gallery
- Montrose Beach
- Garfield Park Conservatory
- Shops at North Bridge
- Goodman Theater
- Tribune Tower
- Chicago Children's Museum
- St. Basil Greek Orthodox Church
- Northwestern Memorial Hospital
- Magnificent Mile Vacations
- Chicago Cultural Center
- Willis Tower
- Garfield Park
- Skydeck Ledge
- Art Institute of Chicago
- Ohio Street Beach
- United Center
- Civic Opera House
- 900 North Michigan Shops
- Chicago Water Tower
- The Salt Shed
- Robie House
- Fisher Building
- Holy Trinity Russian Orthodox Cathedral
- Chase Tower
- Carbide and Carbon Building
- Dave & Buster's
- Mary Bartelme Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.




























