Woodlawn Vacations from $544
Book a Hotel + Flight or Car together to unlock savings
Photo by Tanesha Thompson
- Plan, book, travel with confidence
Better together
Save up to $1,045 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
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.
The Allegro Royal Sonesta Hotel Chicago Loop
Downtown Chicago
Save 100% on your flight
Price was $1,003, price is now $544 per person
$544
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
I enjoyed my stay here
Reviewed on Aug 23, 2025
The Emily Hotel
Downtown Chicago
Price was $1,322, price is now $641 per person
$641
per person
Oct 31 - Nov 5
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug 22, 2025
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $1,267, price is now $636 per person
$636
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,087 reviews)
I give this hotel five stars. A very clean atmosphere. The staff is amazing, the valet workers knew my name, but the best was when I opened that door and seen that window view. It was amazing, gorgeous absolutely beautiful!! I would definitely stay again and tell people what a great experience I had here!
Reviewed on Aug 24, 2025
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,370, price is now $718 per person
$718
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,316 reviews)
Exceptional hotel with ideal location and nice services.
Reviewed on Aug 23, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,106, price is now $1,154 per person
$1,154
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug 19, 2025
Where to stay in Woodlawn
Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn
Downtown Chicago
5 out of top 10 points of interest in this area
The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.
Woodlawn Hotel Deals
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Sep 1 to Sep 2
$177 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (1,211 reviews)
"The room and view were super nice. Even with not being on the waterfront side of the build we werent disappointed. Check in staff could be nicer but the bar staff was excellent. Nice and informative for travelers. The pier was i. Walking distance. Food and shopping all around and spotless insude ..."
Reviewed on Aug 20, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$143 nightly
The price is $168 total per night from Aug 25 to Aug 26
$168 total
Aug 25 - Aug 26
Total with taxes and fees
7.8/10 Good! (8,982 reviews)
"Experience what it must have felt like to attend the 1893 Worlds Fair"
Reviewed on Aug 22, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Sep 3 to Sep 4
$179 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,736 reviews)
"Great location for a quick getaway"
Reviewed on Aug 21, 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.
Discover the most popular places to visit in Woodlawn
Jackson Park
Jackson Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Amble around this vibrant area's lakeside or experience its fascinating museums.
Lorado Taft's Midway Studios
You can find out about the history of Chicago with a stop at Lorado Taft's Midway Studios. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Bob-O-Link Meadow
Enjoy an outing to Bob-O-Link Meadow during your stay in Chicago. Stroll along the lakeside or experience the acclaimed art scene in this vibrant area.
Things to do
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Explore a world of travel with Expedia
Explore a world of travel with Expedia
- Chicago Hotels
- Hotels near Downtown Chicago
- Hotels near Cottage Grove Station
- Cheap Hotels in Chicago
- Hotels near King Drive Station
- Motels in King Drive Station
- Hotels near Lorado Taft's Midway Studios
- Hotels near Midway Plaisance
- Hotels near Oak Woods Cemetery
- Hotels near Hyde Park
- Hotels near University of Chicago
- Hotels near Bond Chapel
- Hotels near Renaissance Society
- Hotels near DuSable Museum of African-American History
- Hotels near Rockefeller Memorial Chapel
- Hotels near Chicago 63rd Street Station
- Hotels near Oriental Institute Museum
- Guest Houses in Chicago 63rd Street Station
- Hotels near Robie House
- Hotels near Nuclear Energy Sculpture
- Cheap Hotels in Hyde Park
- Hotels near Court Theatre
- Hilton Hotels in Hyde Park
- Hotels near Washington Park
- Marriott Hotels & Resorts in Hyde Park
- 3 Star Hotels in Washington Park
- Hotels near 63rd Station
- Hotels near Washington Park
- Hyatt Hotels in Hyde Park
- 4 Star Hotels in Hyde Park
- Hotels with an Indoor Pool in Hyde Park
- Resorts & Hotels with Spas in Hyde Park
- Pet-friendly Hotels in Hyde Park
- 5 Star Hotels in Hyde Park
- Motel 6 Hotels in Hyde Park
- Luxury Hotels in Hyde Park
- Extended Stay America Hotels in Hyde Park
- Hotels with Kitchenettes in Hyde Park
- Hotels with a Pool in Hyde Park
- Hotels with Bars in Hyde Park
- Best Western Hotels in Hyde Park
- Romantic Hotels in Hyde Park
- Historic Hotels in Hyde Park
- Extended Stay Hotels in Hyde Park
- Hotels with Balconies in Hyde Park
- Hotels with a Gym in Hyde Park
- Red Roof Inn Hotels in Hyde Park
- Hotels with Laundry Facilities in Hyde Park
- Hotels with Air Conditioning in Hyde Park
- Casino Hotels in Hyde Park
- Beach Hotels in Hyde Park
- Hotels with Free Breakfast in Hyde Park
- 3 Star Hotels in Hyde Park
- Hotels on the Lake in Hyde Park
- Hotels with Restaurants in Hyde Park
- Hotels with an Outdoor Pool in Hyde Park
- Boutique Hotels in Hyde Park
- La Quinta Inn & Suites Hotels in Hyde Park
- Hotels with Free Parking in Hyde Park
- Sonesta Hotel in Hyde Park
- Family Hotels in Hyde Park
- Hotels with Hot Tubs in Hyde Park
- Club Quarters Hotels in Hyde Park
- Hotel with a Concierge Hotels in Hyde Park
- Affinia Hotels in Hyde Park
- Hotels with Fireplaces in Hyde Park
- Oceanfront Hotels in Hyde Park
- Chicago Museum of Science and Industry
- Lorado Taft's Midway Studios
- Midway Plaisance
- Chicago Vacations
- University of Chicago
- DuSable Museum of African-American History
- Rockefeller Memorial Chapel
- Robie House
- Smart Museum of Art
- Hyde Park Vacations
- Garden of the Phoenix
- Greater Salem Baptist Church
- Jackson Park
- Visit Hyde Park
- Visit Washington Park
- Car rentals near Chicago
- Car rentals near University of Chicago
- Standard Car Rentals near University of Chicago
- Car rentals near Nuclear Energy Sculpture
- Car rentals near Hyde Park
- Enterprise Rental Cars in Hyde Park
- Hertz Rental Cars in Hyde Park
- Budget Rental Cars in Hyde Park
- Avis Rental Cars in Hyde Park
- Rent A Wreck Rental Cars in Hyde Park
- National Car Rental Rental Cars in Hyde Park
- Van Car Rentals in Hyde Park
- First-Car Rental Cars in Hyde Park
- Europcar Rental Cars in Hyde Park
- Minivan Car Rentals in Hyde Park
- Sixt Rental Cars in Hyde Park
- Alamo Rent A Car Rental Cars in Hyde Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.