Woodlawn Holidays from £1,136
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Your Woodlawn Holiday
Book a customized holiday package to Woodlawn and get set to experience its cycling, golfing and walking. However you want to spend your getaway in this green neighbourhood, 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 holiday may look like, you can make it a reality with Expedia.
Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market
Downtown Chicago
£1,348
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
The property was wonderful and the proximity to Fulton Market can't be beat. The staff were always helpful when we had questions and when I faced an unexpected event they were understanding and accommodating. If you are looking for a space where you can spread out, be outdoors, and have beautiful surroundings, I highly recommend Level Fulton Market. We loved the pool and variety of outdoor spaces as well as lounge areas that allowed our group to have separate hang out areas. While you are of course in the heart of the city, the noise fell to the background and we had no issues sleeping or feeling rested. Everything was comfortable and clean. Easy walking to the best dining in the city.
Reviewed on 17 Aug 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
£1,441
per person
19 Oct - 26 Oct
found 1 day ago
Return direct flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,638 reviews)
There need to be more paper-cup for coffee-machine.
Reviewed on 17 Aug 2026
Where to stay in Woodlawn
Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn
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.
The Loop
Bordered roughly by the surrounding elevated train circuit, this Chicago neighborhood has restaurants, galleries, parks and a giant silver bean.
Magnificent Mile
Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.
River North
Known for its fantastic nightlife, stunning river views and popular shops, there's plenty to explore in River North. Top attractions like Merchandise Mart and Bally's Casino Chicago are major draws. Catch the metro at Merchandise Mart Station or Chicago Station (Brown Line) to see more of the city.
Lincoln Park
Both a neighborhood and a park, this northern Chicago area has gorgeous scenery, residential streets lined with stately homes and extensive shopping and dining.
Top hotels in Woodlawn
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
£94
8 Sept - 9 Sept
includes taxes & fees
8/10 Very good! (10,247 reviews)
"Hotel needs to be renovated.. it’s in really rough shape. ..actual spider webs on the windows.. smells bad.. it’s wild.."
Reviewed on 17 Aug 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
£126
30 Aug - 31 Aug
includes taxes & fees
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (859 reviews)
"Loved the check-in and check-out process. Very easy and excellent communication through texts, emails and the Kasa desk in the lobby. The security via the fobs and designated elevators was excellent. The water pressure was good in the shower, and the towels were fluffy. The view in this corner unit ..."
Reviewed on 18 Aug 2026
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 travel package cost?
Our Woodlawn travel packages, which start at just £1,136, are the perfect way to save big. Select your favourite hotels, flights and rental car to create your dream escape.
If I'm not able to travel, can I cancel my Woodlawn travel package?
Yes you can, and we're here to help. You may be able to change or cancel your Woodlawn travel package at no cost within 24 hours of booking. But you may be charged a fee by your airline, hotel or car rental company for older bookings. If your travel plans unexpectedly change, look up our Customer Service Portal for further information.
How do I get a cheap travel package to Woodlawn?
Bundling your flight and hotel with Expedia won't just save precious time — it'll save you money too. A Woodlawn travel package makes it easy to organise the perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your busy schedule won't be a problem. Not only that, we've got over 1,000,000 properties globally to choose from. Now that's what we call choice. Whatever your budget, Expedia brings the world within your reach.
Does Expedia offer Book Now, Pay Later Woodlawn holidays?
Your bank balance shouldn't prevent you from taking a holiday, so Expedia has devised a solution to help. Now that we've joined forces with online lender Klarna, it's easier than ever to book a dream getaway without draining your savings. Klarna offers flexible payment options during the checkout process that take the worry out of budgeting for your escape. Check out these flexible payment options:
- Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make that dream holiday possible.
- Pay in instalments holidays: Into the idea of paying down your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
- Low deposit holidays: If paying a small percentage of your trip (rather than the total upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan from Klarna.
Where should I stay in Woodlawn?
A trip to Woodlawn isn't complete until you've seen Millennium Park and Wrigley Field. Stay somewhere within walking distance for easy access to these popular attractions.
What are the top hotels in Woodlawn?
Book a stay at Hyatt Regency Chicago. It's one of this area's most sought-after hotels. Another well-known option in Woodlawn is The Godfrey Hotel Chicago.
How far in advance should I book my Woodlawn holiday?
It's always wise to book early. Airlines generally release flights nearly 12 months in advance, and this is when you can land some of the cheapest prices. Just been told you need to take your holiday time in a few weeks? That's alright! Expedia are never short on fantastic bargains to whisk you away on the getaway of your dreams, at a price you can afford.
What does an Expedia Woodlawn travel package include?
Select from a combination of rental cars, flights and hotels. Once you've made your booking, you can add activities and tours. Want to pick your fare class? That's easily done too. The choice is yours when it comes to crafting your dream Woodlawn escape.
What should I know before booking a Woodlawn travel package?
So many places to explore, so many things to do. With a package, you'll be able to cross more of them off your list. Combine your flights, rental cars and hotels and get set to save.
Can I choose my airline with a Woodlawn Expedia travel package?
Yes — and it's simple too. Expedia has access to more than 550 partner airlines around the world. Our travel packages give you the freedom to pick from available flights, hotels and activities that fit your needs.
Stay near popular Woodlawn attractions
Jackson Park
7.4/10 (9 reviews)
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.
Obama Presidential Center
You can spend an afternoon browsing the exhibits at Obama Presidential Center in Chicago. Wander the beaches and gardens while you're in the area.
Rubenstein Forum
Learn about the events happening in Rubenstein Forum during your trip to Chicago. Amble around the area's beaches or visit its shops.
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 galleries in this vibrant area.
Jackson Park Driving Range
You can take time to visit Jackson Park Driving Range during your travels to Chicago. Make time to visit the shops and churches while you're in the area.
Things to do
Chicago: Willis Tower Skydeck and The Ledge Ticket
£35
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
£18
per adult
90% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.