Oak Lawn Holidays from £647

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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.
The Allegro Royal Sonesta Hotel Chicago Loop

The Allegro Royal Sonesta Hotel Chicago Loop

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,074, price is now £647 per person
£647
per person
10 Nov - 16 Nov
found 16 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9/10 Wonderful! (1,962 reviews)
The restrooms do not have built in ventilation and the hotel needs to be updated overall.

Reviewed on 25 Aug 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,652, price is now £987 per person
£987
per person
10 Nov - 16 Nov
found 16 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend. Also the coffee bags ? PERFECTION. Just had to add that

Reviewed on 22 Aug 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,028, price is now £1,222 per person
£1,222
per person
10 Nov - 16 Nov
found 16 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
It is a beautiful, well maintained property. The staff is the true gem of the property. They elevate the visitors experience to a new level of excellence.

Reviewed on 25 Aug 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £2,113, price is now £1,322 per person
£1,322
per person
10 Nov - 16 Nov
found 16 hours ago
Return direct 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

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was £1,323, price is now £858 per person
£858
per person
10 Nov - 16 Nov
found 16 hours ago
Return direct flight included
London (LHR) to Chicago (ORD)
9.4/10 Exceptional! (1,059 reviews)
Slow elevators. Solid hotel but nothing spectacular. Would choose other properties in this price point next time.

Reviewed on 26 Aug 2025

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

The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £131 per night from 2 Sept to 3 Sept
£131
2 Sept - 3 Sept
includes taxes & fees
8.2/10 Very Good! (1,219 reviews)
"Friendly"

Reviewed on 24 Aug 2025

The Wade
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 £172 per night from 15 Sept to 16 Sept
£172
15 Sept - 16 Sept
includes taxes & fees
7.8/10 Good! (9,045 reviews)
"Very convenient to South Loop sites!"

Reviewed on 26 Aug 2025

Congress Plaza Hotel
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is £132 per night from 3 Sept to 4 Sept
£132
3 Sept - 4 Sept
includes taxes & fees
8.4/10 Very Good! (4,802 reviews)
"Very nice,everything is around.Highly recommend."

Reviewed on 27 Aug 2025

Embassy Suites by Hilton Chicago Downtown River North
See all 4,660 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
Family Friendly Holidays
Family Friendly Holidays

Popular places to visit

Wrigley Field featuring a city, a sporting event and city views

Wrigley Field

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Magnificent Mile - River North which includes street scenes, signage and night scenes

Michigan Avenue

You can find the perfect gifts to bring home when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Navy Pier

Navy Pier

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

What to do in Oak Lawn

River tour boat in Chicago

Architecture River Tour

£31
per adult
96% of travellers recommend
Architecture River Tour
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 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
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 £647. 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.

* 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.