Oak Lawn Holidays from £719

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Your Oak Lawn Holiday

Experience the unique personality of Oak Lawn with a tailor-made Oak Lawn holiday package. From its welcoming locals to its diversity and beyond, you'll never have a dull moment in this city. Want to explore? SeatGeek Stadium, Chicago Ridge Shopping Mall and Trinity Christian College are just a few of the leading places to visit during your trip to Oak Lawn. Whatever your travel plans or budget, organising a tailored Oak Lawn holiday is a cinch with Expedia.

Top Oak Lawn Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Kimpton Gray Hotel by IHG

Kimpton Gray Hotel by IHG

4.5 out of 5
Downtown Chicago
Price was £898, price is now £719 per person
£719
per person
20 Jan - 24 Jan
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,005 reviews)

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was £1,797, price is now £1,324 per person
£1,324
per person
25 Dec - 30 Dec
found 1 hour ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.6/10 Exceptional! (2,057 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was £1,091, price is now £818 per person
£818
per person
20 Jan - 24 Jan
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on 8 Nov 2026

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

4 out of 5
Downtown Chicago
Price was £1,079, price is now £841 per person
£841
per person
11 Jan - 16 Jan
found 20 hours ago
Return flight included
London (LHR) to Chicago (ORD)
8.6/10 Excellent! (1,009 reviews)

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was £1,202, price is now £955 per person
£955
per person
20 Jan - 24 Jan
found 2 hours ago
Return direct flight included
London (LON) to Chicago (ORD)
9.4/10 Exceptional! (1,309 reviews)
Staff, per usual, went above and beyond. Phenomenal experience every single time. The terrace room, even on pricier days, is better than any other luxury hotel in the city.

Reviewed on 7 Nov 2026

Oak Lawn Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
56,800
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Shedd Aquarium, Field Museum of Natural History and Chicago Museum of Science and Industry

Top hotels in Oak Lawn

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 £103 per night from 22 Nov to 23 Nov
£103
22 Nov - 23 Nov
includes taxes & fees
8/10 Very good! (10,130 reviews)
"The beds are extremely hard and the bathroom floor looked terrible. No water pressure or consistent hot water for the shower. The hotel room doors are extremely old and don’t feel safe. The hallways are very run down. Coming into the hotel they made us use the bell hop to get our luggage in and had ..."

Reviewed on 8 Nov 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is £103 per night from 11 Nov to 12 Nov
£103
11 Nov - 12 Nov
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundable
The price is £102 per night from 6 Dec to 7 Dec
£102
6 Dec - 7 Dec
includes taxes & fees
8.8/10 Excellent! (5,598 reviews)
"Overall amazing!"

Reviewed on 8 Nov 2026

River Hotel
See all 4,498 properties in Oak Lawn
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
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Beach Holidays
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Family Friendly Holidays

Stay near popular Oak Lawn attractions

Chicago Ridge Shopping Mall

7.8/10 (66 reviews)
This bustling retail hub features over 100 stores anchored by Dick's Sporting Goods and Kohl's with SEPHORA. Enjoy premium shopping complemented by diverse dining options and the latest blockbusters at AMC Theatre.
See properties

What to do in Oak Lawn

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

£18
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

£32
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Architecture River Tour from Michigan Avenue

Architecture River Tour from Michigan Avenue

£31
per adult
Architecture River Tour from Michigan Avenue
See all activities in Oak Lawn

Frequently asked questions

How much does an Oak Lawn travel package cost?
Tailor make your Oak Lawn package from as little as £719. Choose from any combination of rental cars, flights and hotels to put together the getaway of your dreams. Don't forget to add on one or two experiences!
If I'm not able to travel, can I cancel my Oak Lawn travel package?
Don't worry if you're rethinking your Oak Lawn travel package — it's possible to change or amend your booking. And if you've booked it within the last 24 hours, you may be able to do it at no cost. However, bookings made more than 24 hours ago may incur charges from your hotel, airline or car rental company. We totally understand life can sometimes throw a spanner in the works, so make your way to our Customer Service Portal if that happens. When you're ready to make changes, we'll be here to help.
How do I get a cheap travel package to Oak Lawn?
Bundle your flights and hotels with Expedia to save big bucks on your next adventure. With more than 550 partner airlines and 1,000,000 hotels around the globe, your Oak Lawn travel package can be tailored exactly to suit your travel style. With all that extra money, why not throw in one or more exciting tours and activities? It's an easy way to unlock even more discounts. The holiday you've always dreamed of in Oak Lawn is much closer than you thought!
Does Expedia offer Book Now, Pay Later Oak Lawn holidays?
We certainly do. Expedia has partnered with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply choose the payment plan that suits best during checkout and take the stress out of budgeting for your trip. Don't forget to bundle your flights, accommodation and car hire with Expedia to get the biggest bang for your buck. Consider these flexible payment options below:

  • Pay monthly holidays: Klarna has convenient monthly payment plans that work for all budgets, so you can escape on that well-deserved holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your trip over multiple transactions.
  • Low deposit holidays: When you stumble on an amazing deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you lock in your escape.

Where should I stay in Oak Lawn?
Close to the action. Many travellers book hotels around popular attractions, like Chicago Ridge Shopping Mall, Childrens Museum of Oak Lawn and Advocate Christ Hospital and Medical Centre.
What are the top hotels in Oak Lawn?
Book a stay at Hyatt Regency Chicago. It's one of this neighbourhood's most in-demand hotels. Another top option in Oak Lawn is The Godfrey Hotel Chicago.
How far in advance should I book my Oak Lawn holiday?
Travellers can normally browse international airfares on Expedia up to a year in advance of departure. Booking late? With a stroke of luck, it's still possible to score an affordable ticket just weeks before your flight.
What does an Expedia Oak Lawn travel package include?
Flights, hotels and car rentals — we bring you the very best deals. All you have to do is pick and choose your favourite combination. After you've made your booking, you can add on the fun stuff like activities and tours. Our travel packages make it simple to put together an awesome Oak Lawn getaway.
What should I know before booking an Oak Lawn travel package?
A travel package can be customized for your circumstances and is a simple way to make your hard-earned dollars stretch further. How much you include is completely up to you. Hotels, rental cars and flights — choose any combination that works with your plans.
Can I choose my airline with an Oak Lawn Expedia travel package?
With a travel package, you're always in charge. Whether you're hoping to fly to Oak Lawn in economy or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines worldwide.

Explore a world of travel with Expedia

* 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.