West Side Vacations from $520
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 $797, price is now $520 per person
$520
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)
I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar.
Reviewed on Jul 1, 2026
Level Chicago - River North
Downtown Chicago
Save 100% on your flight
Price was $1,370, price is now $808 per person
$808
per person
Aug 27 - Sep 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,013 reviews)
This location is ideal for families. The amenities provided are exceptional, scoring a perfect ten out of ten. It offers ample space for a family, including two bathrooms, which was greatly appreciated by my children. The property is well-equipped to ensure a comfortable stay. My only reservation pertains to its distance from Michigan Avenue and the Riverwalk, necessitating a vehicle to access these popular destinations. Otherwise, the experience was flawless.
Reviewed on Jul 2, 2026
Lodge Geneva National
Save 100% on your flight
Price was $1,083, price is now $696 per person
$696
per person
Sep 25 - Sep 29
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (1,375 reviews)
The Lodge is still under renovations. Our room was missing things like a headboard and bedside tables. The water pressure was weak. The amenities were nice for a family stay. It might be great once it’s all done. I wish we knew before booking.
Reviewed on Jun 27, 2026
Level Chicago Fulton Market
Downtown Chicago
Save 100% on your flight
Price was $1,192, price is now $786 per person
$786
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
The staff was extremely friendly and flexible regarding scheduling; this place is amazing.
Reviewed on Jul 1, 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
$179 nightly
The price is $213 total per night from Jul 5 to Jul 6
$213 total
Jul 5 - Jul 6
Total with taxes and fees
9/10 Wonderful! (2,315 reviews)
"Place was okay, definitely wouldn’t book here again. The rooms have a certain hospital odor & the furniture/rooms are really outdated. Definitely gives me early 2000s vibes. We booked last minute since we didn’t want to drink & drive back home. But for any tourist looking for a good place to stay. ..."
Reviewed on Jul 2, 2026
Holiday Inn & Suites Chicago - Downtown by IHG
506 West Harrison Street Chicago IL
Fully refundableReserve now, pay when you stay
$168 nightly
The price is $199 total per night from Jul 6 to Jul 7
$199 total
Jul 6 - Jul 7
Total with taxes and fees
8.6/10 Excellent! (1,045 reviews)
"Nice pool on the roof.Close to everything in the city."
Reviewed on Jul 2, 2026
The Emily Hotel
311 North Morgan Street Chicago IL
Fully refundableReserve now, pay when you stay
$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! (1,319 reviews)
"Very unique motif"
Reviewed on Jul 1, 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.
