Oak Park Vacation Packages 2026 from $272

Oak Park flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Le Méridien Essex Chicago

Downtown Chicago

Save 100% on your flight

$272

per person

Dec 30 - Jan 1

found 2 days ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. A coffee shop, dry cleaning, and luggage storage are also on offer.

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Save 100% on your flight

$567

per person

Dec 19 - Dec 22

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Chicago (ORD)

This smoke-free hotel includes 3 restaurants, an indoor pool, and a 24-hour gym. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.

Harrah's Joliet Hotel & Casino - A Caesars Rewards Destination

$685

per person

Dec 16 - Dec 23

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features 3 restaurants, a bar/lounge, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. A coffee shop, express check-out, and luggage storage are also on offer.

Level Chicago Fulton Market

Downtown Chicago

$637

per person

Jan 24 - Jan 28

found 1 day ago

Roundtrip flight included

Houston (IAH) to Chicago (ORD)

This hotel features a gym and a seasonal outdoor pool. WiFi in public areas is free. Self parking, a business center, and a picnic area are also offered.

Pendry Chicago

Downtown Chicago

Save 100% on your flight

$349

per person

Jan 19 - Jan 22

found 1 day ago

Roundtrip flight included

Dallas (DFW) to Chicago (ORD)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Enjoy the a rooftop terrace and perks like free WiFi. Valet parking, a coffee shop, and a terrace are also offered.

Top Oak Park hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$104 nightly

$124 total

Nov 10 - Nov 11

Total with taxes and fees

This smoke-free hotel's 2 restaurants, 2 bars/lounges, and gym are some of the featured amenities. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a coffee shop, and a hair salon are also offered.

Free WiFi

Restaurant

The Chicago Hotel Collection Ambassador Gold Coast

1301 N State Pkwy Chicago IL

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$159 total

Nov 2 - Nov 3

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. A lobby fireplace, luggage storage, and wedding services are also on offer.

River Hotel

75 East Wacker Drive Chicago IL

Free Cancellation

Reserve now, pay when you stay

$111 nightly

$132 total

Nov 26 - Nov 27

Total with taxes and fees

A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-in, express check-out, and dry cleaning are also on offer.

The Wade

644 N Lake Shore Dr Chicago IL

Free Cancellation

Reserve now, pay when you stay

$119 nightly

$141 total

Nov 23 - Nov 24

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a 24-hour gym on site, and a 24-hour front desk and express check-out are also provided.

The Chicago Hotel Collection - Magnificent Mile

166 E Superior Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$159 total

Nov 1 - Nov 2

Total with taxes and fees

This boutique hotel's 2 restaurants, 2 bars/lounges, and 24-hour gym are some of the featured amenities. Traveling on business? Take advantage of the free WiFi in public areas, express check-out, and valet parking. Enjoy the a rooftop terrace and conveniences like a 24-hour front desk and wedding services.

Hilton Chicago

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$134 nightly

$158 total

Nov 27 - Nov 28

Total with taxes and fees

This smoke-free hotel includes 2 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. You'll appreciate the hot tub, bar/lounge, and snack bar/deli.

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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.

Stay near popular Oak Park attractions

A two-story house with a steeply pitched roof and a brick pathway leading to it.

Frank Lloyd Wright Historic District

9.2/10 (25 reviews)

Visit the birthplace of modern architecture to explore the world's largest collections of homes and buildings designed by Frank Lloyd Wright.

See properties

Frequently asked questions

How much are vacation packages to Oak Park?

Spoil yourself with a memorable experience in Oak Park with a vacation package starting at just $272. Booking your tours, flights and hotels through Travelocity is so easy. What's more, our great deals will leave you with more savings in your pocket for fun times.

How long should my Oak Park vacation be?

Around 2 nights is the average amount of time travelers vacation in Oak Park. But how long is right for you depends on how many cherished memories you want to make. Why not stay a little longer and explore some off-the-beaten-path gems?

Where can I get the best vacation package deals for Oak Park?

Whatever your travel style, Travelocity can help you snap up a great Oak Park package deal. The only thing you have to do is pick and choose between our 400 partner airlines and 1,000,000 worldwide properties.

Why should I book my Oak Park vacation package with Travelocity?

Fantastic savings, countless breathtaking destinations and a team of customer service experts available 24/7 — that's why. And with our Price Match Guarantee, you can rest assured knowing that you'll always get the best possible deal with Travelocity.

Can I save on my Oak Park car rental if I bundle it with my hotel or flight?

You sure can — bundle your flight, hotel and car into an Oak Park vacation package and you'll save a handsome sum. With so much to discover in Oak Park, having your own set of wheels will make exploring a joy. Once you've slid into the driver's seat, get out on the wide open road and head to Six Flags Great America, a top attraction around 35 mi from Oak Park.

Which airport is best for Oak Park?

It's highly likely you'll arrive at O'Hare Intl. Airport (ORD), which is 9 mi northwest of inner Oak Park. Midway Intl. Airport (MDW) (7 mi away from central Oak Park) and Lewis University Airport (LOT) (25 mi away from central Oak Park) are your other options.

What is there to do in Oak Park?

While getting off the beaten track is no doubt rewarding, you shouldn't miss the popular sights that make a place famous. Frank Lloyd Wright Historic District and Unity Temple are just two of them in Oak Park.

Where should I stay when visiting Oak Park?

If you're searching for somewhere to spend your nights, check out the The Write Inn. It's the top choice for many visitors.