Oak Park Vacation Packages 2026 from $449

Oak Park flight + hotel vacation packages

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

Wind Creek Southland Casino and Hotel

East Hazel Crest

$449

per person

Jul 2 - Jul 5

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This resort features a casino, a full-service spa, and 4 restaurants. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Relax with a drink at one of the 3 bars/lounges and enjoy perks like free self parking.

Hotel Riu Plaza Chicago

Downtown Chicago

Save 100% on your flight

$645

per person

Jun 11 - Jun 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Level Chicago Fulton Market

Downtown Chicago

Save 100% on your flight

$1,239

per person

Jun 14 - Jun 21

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A seasonal outdoor pool, self parking, and concierge services are featured at this hotel. WiFi in public areas is free. A business center, a picnic area, and luggage storage are also on offer.

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

Save 100% on your flight

$554

per person

Jun 11 - Jun 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

A gym, valet parking, and free newspapers are featured at this hotel. Business travelers can take advantage of the express check-out. There's dry cleaning and multilingual staff can provide around-the-clock assistance.

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Save 100% on your flight

$775

per person

Jun 11 - Jun 14

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Chicago (ORD)

This 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, laundry service, and valet parking. Self parking, a coffee shop, and a terrace are also offered.

Top Oak Park hotels deals

Hotel Felix River North/Magnificent Mile

111 W Huron St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$125 nightly

$148 total

May 25 - May 26

Total with taxes and fees

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

Pet friendly

Free WiFi

River Hotel

75 East Wacker Drive Chicago IL

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$171 total

May 26 - May 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.

Pet friendly

Free WiFi

Club Quarters Hotel, Central Loop, Chicago

111 West Adams Street Chicago IL

Free Cancellation

$116 nightly

$138 total

May 25 - May 26

Total with taxes and fees

A restaurant and a 24-hour gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A snack bar/deli, express check-in, and express check-out are also on offer.

Pet friendly

Free WiFi

Hilton Chicago/Magnificent Mile Suites

198 E Delaware Pl Chicago IL

Free Cancellation

Reserve now, pay when you stay

$139 nightly

$165 total

May 10 - May 11

Total with taxes and fees

This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Express check-out, dry cleaning, and luggage storage are also on offer.

Pool

Pet friendly

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$151 nightly

$180 total

May 27 - May 28

Total with taxes and fees

This hotel features 2 bars/lounges and a 24-hour gym. Business travelers can take advantage of the free WiFi in public areas. Enjoy a meal from the restaurant and free buffet breakfast each morning.

Breakfast included

Free WiFi

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL

Free Cancellation

Reserve now, pay when you stay

$214 nightly

$251 total

May 23 - May 24

Total with taxes and fees

This hotel features 2 restaurants, a bar/lounge, and A 24-hour gym. Traveling on business? Take advantage of the business center, free WiFi in public areas, and free airport shuttle. You'll appreciate the area shuttle, valet parking, and coffee shop/cafe.

Free airport shuttle

Pet friendly

Don't see what you're looking for?

See all available properties in Oak Park

View all properties

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.

Popular places to visit

Wrigley Field

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

Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

Naval Base Great Lakes

After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.

Navy Pier

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

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 $449. 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.