Woodlawn Holidays from £794

Book a Hotel + Flight or Car together to unlock savings

Photo by Tanesha Thompson

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Packages with flights are ATOL protected

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 - River North

Level Chicago - River North

4 out of 5
Downtown Chicago
per person
3 Oct - 7 Oct
found 1 day ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (654 reviews)
Loved everything. We stayed at Fultom before and the River North is really good as well. Only difference slighty better views with sky terrace at Fulton and from pool side and indoor spa. Riverside has game room which my kid and I enjoyed tons of chess. Great place hard to pick one both has pros and really no cons. Look forward to our next stay. Higher floor the better witb views from the room. Great staff as well!

Reviewed on 15 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
29 Sept - 3 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
One of the best hotels. I will definitely stay here again.

Reviewed on 16 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
29 Sept - 3 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nothing beats a stay at the Park Hyatt when in Chicago!

Reviewed on 10 Aug 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
per person
29 Sept - 3 Oct
found 1 day ago
Return flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (2,063 reviews)
Amazing view and nice stay! Clean & comfortable! Will come back again!

Reviewed on 16 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
per person
4 Oct - 11 Oct
found 1 day ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
The hotel is situated in Fulton market and has many options for dining. The bed was comfortable, but the linens were very wrinkled and the comforter had stains on it.

Reviewed on 15 Aug 2025

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 £163 per night from 14 Sept to 15 Sept
£163
14 Sept - 15 Sept
includes taxes & fees
7.8/10 Good! (8,984 reviews)
"Great location! Quiet and comfortable room. Love the history and architectural charm of this classic Chicago Hotel! Exercise room was the best equipped I've used!"

Reviewed on 14 Aug 2025

Congress Plaza Hotel
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 £169 per night from 4 Sept to 5 Sept
£169
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (1,852 reviews)
"Pleasant experience. Accommodations were good. Surrounding area was convenient to shopping, eateries and p parks."

Reviewed on 13 Aug 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 25 Aug to 26 Aug
£132
25 Aug - 26 Aug
includes taxes & fees
8.4/10 Very Good! (3,675 reviews)
"Hotel was quiet. Room was comfortable. Location was great."

Reviewed on 13 Aug 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 4,468 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Woodlawn travel package cost?
Our Woodlawn travel packages, which start at just £794, 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.

Things to do

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

£33
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

£30
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture 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. Flight-inclusive packages are ATOL protected.