Woodlawn Vacations

Book a Hotel + Flight or Car together to unlock savings

Photo by Richard Remington

Your Woodlawn Vacation

Book a customized vacation package to Woodlawn and get set to experience its cycling, golfing and walking. However you want to spend your getaway in this green neighborhood, there are plenty of opportunities for both adventure and relaxation. Some nearby attractions to visit during your trip to Woodlawn include University of Chicago, Chicago Museum of Science and Industry and Robie House. Whatever your ideal Woodlawn vacation may look like, you can make it a reality with Expedia.

The Latest Woodlawn Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Aloft Chicago Downtown River North

Aloft Chicago Downtown River North

3.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,028 reviews)
Had everything I needed in walking distance, felt like the Hotel had everything I needed.

Reviewed on May 29, 2024

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 29
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (1,001 reviews)
They didn’t have free wifi

Reviewed on May 28, 2024

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 17 - Aug 20
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.8/10 Excellent! (208 reviews)
Loved all the neighborhood dogs & farmers market

Reviewed on May 20, 2024

The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 25 - Aug 29
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,136 reviews)
Close go downtown tourist sites.

Reviewed on May 27, 2024

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
Aug 18 - Aug 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,200 reviews)
This is the nicest hotel in Chicago

Reviewed on May 31, 2024

Where to stay in Woodlawn

Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn
Downtown Chicago showing a city

Downtown Chicago

4 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.

Find hotel + flight trips in Downtown Chicago

Woodlawn Hotel Deals

Congress Plaza Hotel
Congress Plaza Hotel
3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $188 per night from Jun 16 to Jun 17
$188
$221 total
includes taxes & fees
Jun 16 - Jun 17
7.6/10 Good! (6,816 reviews)
"Be aware there is only Analog TV in the room"

Reviewed on May 29, 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundable
The price is $166 per night from Jul 2 to Jul 3
$166
$195 total
includes taxes & fees
Jul 2 - Jul 3
8.6/10 Excellent! (2,912 reviews)
"The facility was beautiful. The staff was extremely friendly and helpful. The views of the city were phenomenal."

Reviewed on May 28, 2024

River Hotel
Eurostars Magnificent Mile
Eurostars Magnificent Mile
4 out of 5
660 North State Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is $170 per night from Jun 30 to Jul 1
$170
$200 total
includes taxes & fees
Jun 30 - Jul 1
8.4/10 Very Good! (1,993 reviews)
"We stayed for a weekend get a way and it was perfect."

Reviewed on May 31, 2024

Eurostars Magnificent Mile
See all 4,020 properties in Woodlawn
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Woodlawn vacation package cost?
Our Woodlawn packages, which start at just $247, are the best way to save. Pick your favorite hotels, flights and rental car to create your dream itinerary.
How do I get a cheap travel package to Woodlawn?
Bundle your hotels and flights with Expedia to save on your next exciting adventure. With over 550 partner airlines and 1,000,000 hotel options worldwide, your Woodlawn vacation package can be tailored exactly to suit your budget. With all those extra dollars, why not throw in a few exciting tours and activities? It’s an easy way to unlock even more savings. That vacation you’ve always dreamed of in Woodlawn is closer than you thought!
Where should I stay in Woodlawn?
Most travelers who visit Woodlawn include University of Chicago and Chicago Museum of Science and Industry on their bucket lists. Why not choose a hotel that’s close to these fantastic attractions?
How far in advance should I book my Woodlawn vacation?
Browse Expedia to compare international airfares as early as possible. You can generally purchase a ticket up to 12 months prior to departure. If you don’t see your preferred carrier, or you’ve left things to the last minute, fear not. Low prices to Woodlawn sometimes appear just weeks before the date of departure.
What does an Expedia Woodlawn travel package include?
Flights, hotels and rental cars — we have them well covered. With Expedia, you can create your Woodlawn package however you want. All you have to do is figure out just what you need. Once you’ve made your booking, you can add extras like activities and tours. The more you bundle, the greater the savings!
What should I know before booking a Woodlawn travel package?
Whether it’s relaxation or adventure you’re after, a Woodlawn vacation package lets you organize your escape your way. Plus, you’ll get access to great discounts just for combining your accommodations with your rental car and flights. The more you bundle, the more you’ll save!
Can I choose my airline with a Woodlawn Expedia vacation package?
Expedia offers access to more than 550 partner airlines worldwide, so you sure can! Simply choose your preferred air carrier and create your ideal Woodlawn vacation.
If I'm not able to travel, can I cancel my Woodlawn vacation package?
Yes you can, and we’ll help you every step of the way. You may be able to cancel or change your Woodlawn vacation package at no cost if you booked in the last 24 hours. However, you may incur a fee from your airline, hotel or car rental company for older bookings. If your travel plans unexpectedly change, visit our Customer Service Portal for more information.

Discover the most popular places to visit in Woodlawn

Image for Jackson Park

Jackson Park

4/5(7 reviews)

Explore the great outdoors at Jackson Park, a lovely green space in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.

Jackson Park
Image for 63rd Street Beach

63rd Street Beach

Why not spend a lazy afternoon at 63rd Street Beach during your trip to Chicago? Wander the beaches and gardens while you're in the area.

63rd Street Beach
Image for Lorado Taft's Midway Studios

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 fascinating museums in this vibrant area.

Lorado Taft's Midway Studios

Things to do

Image for Odyssey Lake Michigan Premier Dinner Cruise

Odyssey Lake Michigan Premier Dinner Cruise

$188
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Chicago Architecture Center River Cruise aboard Chicago's First Lady

Chicago Architecture Center River Cruise aboard Chicago's First Lady

$54
Per adult
94% of travellers recommend
Chicago Architecture Center River Cruise aboard Chicago's First Lady
Image for Chicago Pizza Tour

Chicago Pizza Tour

$89
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

Other vacations you might like

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.