Woodlawn Holidays from AU$2,214

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Your Woodlawn Holiday

From its cycling to its golfing and walking, there are tons of convincing reasons to book a holiday package to Woodlawn. When you're ready to escape the everyday, this green neighbourhood 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 holiday now.

Top Holiday Package Deals in Woodlawn

Price found within the past 48 hours. Click for updated prices.
Economy Inn By Townhouse Merrillville US 30

Economy Inn By Townhouse Merrillville US 30

2.5 out of 5
Price was AU$2,501, price is now AU$2,214 per person
AU$2,214
per person
14 Feb - 21 Feb
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
6/10 (4 reviews)
Need carpet in the rooms .. have more cold days then hot .. carpet and updated lighting would make it cozy

Reviewed on 11 Oct 2025

Hilton Garden Inn Merrillville

Hilton Garden Inn Merrillville

3 out of 5
Green Acres
Price was AU$2,738, price is now AU$2,395 per person
AU$2,395
per person
14 Feb - 21 Feb
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,000 reviews)
Expensive for the amenities and area

Reviewed on 13 Dec 2025

Wind Creek Southland Casino and Hotel

Wind Creek Southland Casino and Hotel

4 out of 5
East Hazel Crest
Price was AU$3,130, price is now AU$2,754 per person
AU$2,754
per person
14 Feb - 21 Feb
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (MDW)
9.4/10 Exceptional! (160 reviews)
It was relaxing and fun for the kids

Reviewed on 5 Jan 2026

Ameristar Casino Hotel East Chicago

Ameristar Casino Hotel East Chicago

4 out of 5
Price was AU$2,729, price is now AU$2,471 per person
AU$2,471
per person
14 Feb - 21 Feb
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
8.4/10 Very Good! (1,004 reviews)
Helpful people at the front desk and nice lady fro housekeeping

Reviewed on 18 Dec 2025

Capital O Elite Inn & Suites South Holland I 94

Capital O Elite Inn & Suites South Holland I 94

2.5 out of 5
Price was AU$2,440, price is now AU$2,219 per person
AU$2,219
per person
14 Feb - 21 Feb
found 3 hours ago
Return flight included
Sydney (SYD) to Chicago (ORD)
6.6/10 (78 reviews)
The hotel created a calm impression right from the entrance. The room was clean and arranged in a comfortable way. Staff members were polite and easy to approach. The overall stay felt smooth and relaxing.

Reviewed on 28 Dec 2025

Our guide on 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

Our pick of the best Woodlawn Hotel Deals

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 AU$156 per night from 12 Jan to 13 Jan
AU$156
12 Jan - 13 Jan
includes taxes & fees
8.8/10 Excellent! (3,668 reviews)
Great hotel!

Reviewed on 5 Jan 2026

Hilton Chicago/Magnificent Mile Suites
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$286 per night from 13 Jan to 14 Jan
AU$286
13 Jan - 14 Jan
includes taxes & fees
8.4/10 Very Good! (2,494 reviews)
I paid for a king room and had that for the first half of my stay, but something went wrong with the water heater for the floor(?). It wasn't explained well to us, but we were moved into another room on a higher level which I assumed would have been similar but it was much smaller and had a queen ...

Reviewed on 5 Jan 2026

Hilton Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Fully refundableReserve now, pay when you stay
The price is AU$287 per night from 13 Jan to 14 Jan
AU$287
13 Jan - 14 Jan
includes taxes & fees
8.4/10 Very Good! (2,206 reviews)
The hotel restaurant was delicious

Reviewed on 2 Jan 2026

Palmer House a Hilton Hotel
See all 4,609 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.
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Frequently asked questions

How much does a Woodlawn holiday package cost?
Our Woodlawn packages, which start at just AU$2,214, 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.

Discover the most popular places to visit in Woodlawn

Jackson Park

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 acclaimed art galleries.

Jackson Park

Activities

Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

AU$60
per adult
92% of travellers recommend
Art Institute of Chicago
Lineup with Capone and Dillinger!

Chicago Crime and Mob Bus Tour

AU$73
per adult
92% of travellers recommend
Chicago Crime and Mob Bus Tour
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.