Woodlawn Holidays from £1,035

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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.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was £1,319, price is now £1,035 per person
£1,035
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
8.2/10 Very good! (2,797 reviews)
I would definitely stay here again! Convenient location, walkable from most things. Staff were amazing and so helpful. Basic rooms, decent size. Very clean, great bar.

Reviewed on 1 Jul 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was £2,570, price is now £1,829 per person
£1,829
per person
23 Aug - 29 Aug
found 1 day ago
Return flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (504 reviews)
The staff was extremely friendly and flexible regarding scheduling; this place is amazing.

Reviewed on 1 Jul 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was £1,629, price is now £1,268 per person
£1,268
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.2/10 Wonderful! (1,323 reviews)
Very unique motif

Reviewed on 1 Jul 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was £1,652, price is now £1,309 per person
£1,309
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.4/10 Exceptional! (2,554 reviews)
Excellente

Reviewed on 1 Jul 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,939, price is now £1,546 per person
£1,546
per person
4 Sept - 8 Sept
found 1 day ago
Return flight included
Edinburgh (EDI) to Chicago (ORD)
9.6/10 Exceptional! (1,899 reviews)
Great service

Reviewed on 30 Jun 2026

Where to stay in Woodlawn

Find the best Woodlawn areas and neighborhoods for the activities you enjoy most. Learn more about Woodlawn
A busy city street with tall buildings, a bus, and cars.

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 £109 per night from 6 Jul to 7 Jul
£109
6 Jul - 7 Jul
includes taxes & fees
8/10 Very good! (10,190 reviews)
"The rooms were bigger than expected! Very nice hotel and helpful staff. We arrived early than check in time was able to check in early for a fee. They had staff everywhere whom were very helpful with directions or if need any type of transportation. This was my second time staying here. Great location ..."

Reviewed on 2 Jul 2026

Congress Plaza Hotel
Omni Chicago Hotel

Omni Chicago Hotel

4.5 out of 5
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is £162 per night from 5 Jul to 6 Jul
£162
5 Jul - 6 Jul
includes taxes & fees
9.2/10 Wonderful! (1,828 reviews)
"Very nice hotel. Great location, nice sized rooms."

Reviewed on 2 Jul 2026

Omni Chicago Hotel
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is £171 per night from 7 Jul to 8 Jul
£171
7 Jul - 8 Jul
includes taxes & fees
8.8/10 Excellent! (2,769 reviews)
"We like that the airport was close to the hotel, the check-in staff is not really that helpful in the breakfast is not complementary. The lobby in the rooms are very nice, but again the hotel is a little bit complicated to navigate out of the parking lot. Many Chicago hotels charge for parking daily ..."

Reviewed on 2 Jul 2026

Hyatt Regency O'Hare Chicago
See all 4,303 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
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Family Friendly Holidays

Frequently asked questions

How much does a Woodlawn travel package cost?
Our Woodlawn travel packages, which start at just £1,035, 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 fascinating museums.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

£18
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.