Woodlawn Vacations from $289
Book a Hotel + Flight or Car together to unlock savings
Your Woodlawn Vacation
From its cycling to its golfing and walking, there are tons of convincing reasons to book a vacation package to Woodlawn. When you're ready to escape the everyday, this green neighborhood is calling. Wondering what to see and do during your trip to Woodlawn? Nearby attractions such as University of Chicago, Chicago Museum of Science and Industry and Robie House are good places to begin. Expedia will help put your plans into action. Book your perfect Woodlawn vacation now.
The Latest Woodlawn Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Price was $639, price is now $440 per person
$440
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.
Reviewed on Nov 8, 2026
The Emily Hotel
Downtown Chicago
Price was $922, price is now $649 per person
$649
per person
Jan 15 - Jan 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.
Reviewed on Nov 13, 2026
Where to stay in Woodlawn
Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn
Downtown Chicago
4 out of top 10 points of interest in this area
Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.
Woodlawn Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $127 total per night from Nov 22 to Nov 23
$127 total
Nov 22 - Nov 23
Total with taxes and fees
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $138 total per night from Nov 15 to Nov 16
$138 total
Nov 15 - Nov 16
Total with taxes and fees
River Hotel
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $117 total per night from Dec 10 to Dec 11
$117 total
Dec 10 - Dec 11
Total with taxes and fees
8.8/10 Excellent! (5,606 reviews)
"The room was small but cozy and clean. The elevator could be faster. The area was secure and walking distance from a lot of sites. I really recommend it."
Reviewed on Nov 13, 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.
Stay near popular Woodlawn attractions
Things to do
Chicago's Navy Pier Centennial Wheel Ticket
$24
per adult
100% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Explore a world of travel with Expedia
- Hilton Hotels in Hyde Park
- Hyde Park Hotels
- Budget Hotels in Hyde Park
- 5 Star Hotels in Hyde Park
- Cabins in Chicago
- Marriott Hotels & Resorts Hotels in Hyde Park
- South Shore Hotels
- Luxury Hotels in Hyde Park
- Motels in Chicago
- 4 Star Hotels in Chicago
- Chinatown Hotels
- South Loop Hotels
- South Chicago Hotels
- Bronzeville Hotels
- Flights from Atlanta (ATL) to Chicago (MDW)
- Flights to Chicago
- Delta Air Lines Atlanta (ATL) to Chicago (MDW) flights
- Flights from Los Angeles (LAX) to Chicago (MDW)
- Flights to Midway Intl.
- Porter Airlines Toronto (YTZ) to Chicago (MDW) flights
- Flights to Bridgeview
- Flights to Alsip
- Flights to Oak Lawn
- Flights to Berwyn
- Robie House
- Visit Hyde Park
- Where to stay in Chicago
- Chicago All Inclusive Vacation Packages
- Griffin Museum of Science and Industry
- Visit The Loop
- Chicago All Inclusive Vacation Packages
- Where to stay in North Pullman
- Art Institute of Chicago
- Visit Downtown Chicago
- Where to stay in South Side
- Chicago Vacations
- Visit South Loop
- Where to stay in Cicero
- Grant Park
- Visit West Loop
- Where to stay in Bridgeview
- Downtown Chicago Vacations
- Visit Canaryville
- Central Chicago All Inclusive Vacation Packages
- Where to stay in Tinley Park
- Oak Park Vacations
- Blue Island Vacations
- Westchester Vacations
- Rosemont Vacations
- Bridgeview Vacations
- Summit Vacations
- Burbank Vacations
- Hometown Vacations
- Chicago All Inclusive Vacation Packages
- Chicago All Inclusive Vacation Packages
- Chicago All Inclusive Vacation Packages
- Visit Magnificent Mile
- Chicago All Inclusive Vacation Packages
- Where to stay in Oakbrook Terrace
- Visit Rush Street
- Central Chicago All Inclusive Vacation Packages
- Where to stay in Central Chicago
- Visit United Center
- Central Chicago All Inclusive Vacation Packages
- Where to stay in Evanston
- Visit Lincoln Park
- South Side All Inclusive Vacation Packages
- Where to stay in Alsip
- Visit Streeterville
- Far Southeast Side All Inclusive Vacation Packages
- Hertz Rental Cars in Hyde Park
- Car rentals near Hyde Park
- Minivan Car Rentals in Chicago
- Enterprise Rental Cars in Hyde Park
- Car rentals near Woodlawn
- Van Car Rentals in Midway Intl.
- Car rentals near South Loop
- SUV Car Rentals in Chicago
- Car rental Airport (MDW)
- Car rentals in Evergreen Park
- Car rentals near Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.