Woodlawn Packages (Flight + Hotel)

Book a Hotel + Flight or Car together to unlock savings

Photo by Tanesha Thompson

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    Better together

    Save up to ฿4,531 when you book a flight and hotel together*
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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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Where to stay in Woodlawn

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

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.

Find hotels in Downtown Chicago

Top hotels in Woodlawn

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 ฿5,745 per night from 4 Aug to 5 Aug
฿5,745
฿6,744 total
4 Aug - 5 Aug
includes taxes & fees
7.8/10 Good! (8,992 reviews)
"Hotel was beautiful"

Reviewed on 27 Jul 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is ฿7,903 per night from 22 Aug to 23 Aug
฿7,903
฿10,313 total
22 Aug - 23 Aug
includes taxes & fees
9/10 Wonderful! (2,129 reviews)
Overall a great family hotel
"Great time in Chicago and the hotel made it phenomenal! It’s in a very central location and allows access to all the major tourist attractions within walking distance. We really enjoyed Saturday movie night at the pool!"

Reviewed on 28 Jul 2025

InterContinental Chicago Magnificent Mile by IHG
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿4,653 per night from 17 Aug to 18 Aug
฿4,653
฿5,462 total
17 Aug - 18 Aug
includes taxes & fees
8.8/10 Excellent! (2,548 reviews)
"Great area, clean hotel but, parking is expensive. There was no pool."

Reviewed on 27 Jul 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,484 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.

Frequently asked questions

How much does a Woodlawn holiday package cost?
Our Woodlawn packages, which start at just , are the best way to save. Pick your favourite 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 holiday 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 holiday you've always dreamed of in Woodlawn is closer than you thought!
Where should I stay in Woodlawn?
Most travellers 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 holiday?
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 holiday package lets you organise your escape your way. Plus, you'll get access to great discounts just for combining your accommodation with your rental car and flights. The more you bundle, the more you'll save!
Can I choose my airline with a Woodlawn Expedia holiday 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 holiday.
If I'm not able to travel, can I cancel my Woodlawn holiday package?
Yes you can, and we'll help you every step of the way. You may be able to cancel or change your Woodlawn holiday 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.

Things to do

River tour boat in Chicago

Architecture River Tour

฿1,345
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

฿1,314
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

฿1,460
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.