Oak Park Vacation Packages 2026 from $302

Oak Park flight + hotel vacation packages

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

Holiday Inn Chicago - Schaumburg by IHG

Save 100% on your flight

$302

per person

Apr 8 - Apr 12

found 1 day ago

Roundtrip non-stop flight included

Tampa (TPA) to Chicago (ORD)

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.

Hotel Felix River North/Magnificent Mile

Downtown Chicago

Save 100% on your flight

$405

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Chicago (ORD)

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.

Level Chicago – Old Town

Downtown Chicago

$532

per person

Apr 17 - Apr 21

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Chicago (ORD)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. There's fun for all ages with a playground and an arcade/game room, and barbecue grills are available on site. Enjoy the a rooftop terrace and perks like free WiFi.

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

$911

per person

Apr 17 - Apr 21

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Chicago (ORD)

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the express check-out, laundry service, and valet parking. There's luggage storage and multilingual staff can provide around-the-clock assistance.

The Emily Hotel

Downtown Chicago

Save 100% on your flight

$640

per person

Apr 15 - Apr 19

found 1 day ago

Roundtrip flight included

Baltimore (BWI) to Chicago (ORD)

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, laundry service, and valet parking. A coffee shop, a snack bar/deli, and luggage storage are also on offer.

Top Oak Park hotels deals

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$97 nightly

$114 total

Jan 31 - Feb 1

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

Embassy Suites by Hilton Chicago Downtown River North

600 N State St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$107 nightly

$125 total

Feb 8 - Feb 9

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and free full breakfast each morning. Valet parking, a business center, and a grocery/convenience store are also offered.

Pool

Breakfast included

Hotel Riu Plaza Chicago

150 East Ontario Street Chicago IL

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$156 total

Feb 9 - Feb 10

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

720 S Michigan Ave Chicago IL

Free Cancellation

Reserve now, pay when you stay

$155 nightly

$182 total

Feb 5 - Feb 6

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.

Pool

Hot Tub

DoubleTree by Hilton Chicago - Magnificent Mile

300 E Ohio St Chicago IL

Free Cancellation

Reserve now, pay when you stay

$85 nightly

$100 total

Feb 5 - Feb 6

Total with taxes and fees

This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. You'll appreciate the gym, poolside bar, and concierge services.

Pool

Pet friendly

Pendry Chicago

230 North Michigan Avenue Chicago IL

Free Cancellation

Reserve now, pay when you stay

$205 nightly

$241 total

Feb 12 - Feb 13

Total with taxes and fees

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.

Pet friendly

Free WiFi

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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.

Popular places to visit

Wrigley Field

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

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

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 $302. 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.