Woodlawn Packages (Flight + Hotel)

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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

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

Top hotels in Woodlawn

Warwick Allerton - Chicago
Warwick Allerton - Chicago
4 out of 5
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿4,558 per night from 27 May to 28 May
฿4,558
per night
27 May - 28 May
7.6/10 Good! (2,598 reviews)
"I don’t really write reviews for places I stay at but this one impressed me beyond my expectations. I planned this trip for my fiancé’s 30th birthday and the location and price of this hotel is the best you will find. Not too far away from everything, conveniently located transportation and so many ..."

Reviewed on 20 May 2024

Warwick Allerton - Chicago
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 ฿5,419 per night from 27 May to 28 May
฿5,419
per night
27 May - 28 May
7.6/10 Good! (6,777 reviews)
"Looks like old antique hotel. It was quiet and felt very safe."

Reviewed on 21 May 2024

Congress Plaza Hotel
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ฿5,162 per night from 27 May to 28 May
฿5,162
per night
27 May - 28 May
8.6/10 Excellent! (2,887 reviews)
"Nice hotel and location"

Reviewed on 20 May 2024

River Hotel
See all 3,999 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.

Popular places to visit

Image for Jackson Park

Jackson Park

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 galleries.

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 when you stop by 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

฿5,313
Per adult
76% of travellers recommend
Odyssey Lake Michigan Premier Dinner Cruise
Image for Spirit of Chicago Signature Dinner Cruise on Lake Michigan

Spirit of Chicago Signature Dinner Cruise on Lake Michigan

฿5,775
Per adult
Spirit of Chicago Signature Dinner Cruise on Lake Michigan
Image for Chicago Pizza Tour

Chicago Pizza Tour

฿2,643
Per adult
100% of travellers recommend
Chicago Pizza Tour
See all activities in Chicago

More trip options

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