Deals on vacations and trips to Oak Park

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Oak Park flight + hotel vacation packages

Fairmont Chicago at Millennium Park Gold Experience

Fairmont Chicago at Millennium Park Gold Experience

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 28 - Jun 1
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. A bar/lounge, a 24-hour front desk, and express check-in are also provided.
JW Marriott Chicago

JW Marriott Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 25 - May 28
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this luxury hotel. Traveling on business? Take advantage of the business center, express check-in, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 25 - May 28
Roundtrip flight included
Atlanta (ATL) 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.
Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 25 - May 28
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this eco-certified hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. You'll appreciate the indoor pool, bar/lounge, and laundry facilities.
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 25 - May 28
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Families will appreciate the onsite laundry facilities, kid-friendly dining, and in-room childcare. Enjoy the gym and perks like free WiFi.
Prices and availability subject to change. Additional terms may apply.

Top Oak Park hotel deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $127 per night
$127
per night
Apr 29 - Apr 30
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.
Breakfast available
Free WiFi
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $139 per night
$139
per night
Apr 28 - Apr 29
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
Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
660 North State Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $160 per night
$160
per night
Apr 28 - Apr 29
A full-service spa and a gym are featured at this boutique hotel. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and valet parking. There's a sauna on site, and a 24-hour front desk and express check-out are also provided.
Spa
Free WiFi
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $82 per night
$82
per night
Apr 29 - Apr 30
This hotel features a 24-hour gym and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a lobby fireplace, and a communal living room are also offered.
Pet friendly
Free WiFi
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $129 per night
$129
per night
Apr 28 - Apr 29
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
Breakfast available
Aloft Chicago Mag Mile

Aloft Chicago Mag Mile

3 out of 5
243 E. Ontario, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
The price is $102 per night
$102
per night
Apr 28 - Apr 29
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the gym and perks like free WiFi. Valet parking, a business center, and a snack bar/deli are also offered.
Pet friendly
Breakfast available
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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

Image for Wrigley Field

Wrigley Field

4.5/5(2,128 reviews)

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

Wrigley Field
Image for McCormick Place

McCormick Place

4.5/5(1,805 reviews)

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.

McCormick Place
Image for Navy Pier

Navy Pier

4.5/5(4,870 reviews)

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

Navy Pier

Frequently asked questions

How much are vacation packages to Oak Park?
Packages, including flights and hotels in Oak Park, start from $401. Make your daydreams come true and lock in your trip with Travelocity today.
How long should my Oak Park vacation be?
Around 2 nights is the average time frame travelers vacation in Oak Park. But how long is right for you comes down to how many treasured memories you want to make. Why not allow a few extra days and explore some hidden gems?
Where can I get the best vacation package deals for Oak Park?
There are fantastic Oak Park package deals to be scored with Travelocity. Did you know we partner with 400 airlines and 1,000,000 properties all over the world? Remember this the next time you’re ready to tick another destination off your list.
Why should I book my Oak Park vacation package with Travelocity?
From our 24/7 customer care to our range of incredible destinations, we’re dedicated to giving you the most unforgettable vacation. All you’ll have to do is to click and book — our Price Match Guarantee will ensure you score the best deal.
Will I save money on my Oak Park car rental if I book it with hotels and flights?
With an Oak Park vacation package, you can bundle your hotel, flight and car bookings and save a ton. If you’d love to discover the best of this fabulous region, why not head to Six Flags Great America? This well-known sight is 35 mi from Oak Park. With your own set of wheels, you’ll be there in a jiffy.
What is the best time of year to go to Oak Park?
If a tight budget is what’s driving your travel decisions, you’ll get the best deals in . is generally the costliest month. Most travelers come to this location during January, March and June. If you want to avoid peak season, you’ll find it more peaceful in August, October and December.
Which airport is best for Oak Park?
O’Hare Intl. Airport (ORD) is one of the busiest airports in Oak Park. It’s located 9 mi northwest of the bustling downtown area. Your other choices are Midway Intl. Airport (MDW) (7 mi away from central Oak Park) and Lewis University Airport (LOT) (25 mi away from central Oak Park).
What is there to do in Oak Park?
While taking the path less traveled can be rewarding, you really shouldn’t miss the well-known sights that make a destination famous. Frank Lloyd Wright Historic District and Ernest Hemingway Museum and House are just two of them in Oak Park.
Where should I stay when visiting Oak Park?
If you’re after a place to base yourself, check out the The Write Inn. It’s the top pick for many visitors.