Oak Park Vacation Packages

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Your Oak Park Vacation

With one of our vacation packages to Oak Park, you'll have endless opportunities for adventure and relaxation. There's a lot to experience, including its chic vibe and rich history. Want to explore your new surroundings? United Center, Brookfield Zoo and Portage Park are just three of the leading places to visit during your trip to Oak Park. No matter your travel plans or budget, putting together the ultimate tailored Oak Park vacation is a walk in the park with Expedia.

Top Oak Park Vacation Deals

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
per person
May 9 - May 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,988 reviews)
For it being my first time staying at this hotel, I wasn’t sure what to expect but it was fantastic. Front desk service was efficient, and the room was clean! I loved the layout of the room, and received the privacy I wanted. Would definitely book again.

Reviewed on Mar. 28, 2025

Dorothy's

Dorothy's

3 out of 5
Lakeview
Save 100% on your flight
per person
May 14 - May 17
found 1 day ago
Roundtrip non-stop flight included
Calgary (YYC) to Chicago (ORD)
8.4/10 Very Good! (24 reviews)
We love Dorothy's! This is such a great, inexpensive option for a stay in a fantastic neighborhood. Would recommend to anyone!

Reviewed on Mar. 8, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
per person
May 16 - May 19
found 10 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
Nice swimming pool for lap swimming.

Reviewed on Mar. 23, 2025

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
per person
Jun. 5 - Jun. 8
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,309 reviews)
I love this property for St Patricks day events (weekend before). Have stayed in it twice now during this holiday. It’s clean, the staff is very nice. However, losing cold water that morning when everyone is preparing for the events was not enjoyable. Hot water didn’t come back until the afternoon/evening.

Reviewed on Mar. 26, 2025

The Chicago Hotel Collection - Wrigleyville

The Chicago Hotel Collection - Wrigleyville

3.5 out of 5
Lakeview
Save 100% on your flight
per person
May 30 - Jun. 2
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
6.6/10 (735 reviews)
Pretty average stay! Thin walls so expect to hear doors closing and people talking a

Reviewed on Mar. 25, 2025

Ready to book your vacation to Oak Park?

 

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Oak Park Hotel Deals

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 CA $181 per night from Apr. 13 to Apr. 14
CA $181
CA $213 total
includes taxes & fees
Apr 13 - Apr 14
8.2/10 Very Good! (3,756 reviews)
"This is a great property for families. It had a large breakfast area. A lot of places to hang out outside of the room. The view from the room was great too."

Reviewed on Mar. 24, 2025

Embassy Suites by Hilton Chicago Downtown River North
River Hotel
River Hotel
4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $141 per night from Apr. 20 to Apr. 21
CA $141
CA $166 total
includes taxes & fees
Apr 20 - Apr 21
8.6/10 Excellent! (3,948 reviews)
"What we really liked about the rooms at The River Hotel was how the two beds were in separate rooms, though it’s not a true suite. Having two bathrooms in a standard room is great, too, especially when traveling with teens. The front desk staff was fantastic including the valet."

Reviewed on Mar. 25, 2025

River Hotel
Crowne Plaza Chicago West Loop by IHG
Crowne Plaza Chicago West Loop by IHG
3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $132 per night from Apr. 6 to Apr. 7
CA $132
CA $155 total
includes taxes & fees
Apr 6 - Apr 7
8.6/10 Excellent! (1,004 reviews)
"People at the front desk were very kind and easy to check in. Room was very nice, clean, and comfortable."

Reviewed on Mar. 25, 2025

Crowne Plaza Chicago West Loop by IHG
See all 4,512 properties in Oak Park
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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does an Oak Park vacation package cost?
Offering great value package deals from CA $554 on Expedia, you’ll be pleasantly surprised at how much a vacation to Oak Park costs! Expedia’s packages make travel planning easier and your savings go further.
What are the cheapest months to go to Oak Park?
You can usually find reduced prices and greater availability in January, February and March. Take a look at our cheap Oak Park vacation packages and you could score some great off-season discounts.
How many days is enough for Oak Park?
Dedicate at least 2 days for your Oak Park vacation in order to discover everything that makes this place unique. Wander around key neighborhoods, including Illinois Medical District and West Town. Then check out major sights like Unity Temple and Oak Park Conservatory. With a clever itinerary, you’ll be kept busy with room for some me-time too. Want to go beyond Oak Park? Consider squeezing in an excursion or two.
Is it worth booking a vacation package to Oak Park?
During your Oak Park vacation, you can look forward to enjoying some excellent history and culture. Leave enough room in your schedule to visit leading attractions like Unity Temple and Madison Street Theatre.
How to find the best Oak Park package deals?
Begin your search for an Oak Park package deal by entering your destination and preferred trip dates under our “Packages” tab. Then select a few filters, like “Guest rating” and “Property type,” to tailor the results to your exact needs. You can also sort by “Package discount” and discover offers that come with huge savings. If you don’t find the perfect Oak Park package deal straight away, just play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Oak Park escape off to a flying start.
Is it cheaper to book an Oak Park vacation as a package?
You can enjoy significant savings on your next Oak Park getaway by booking a personalized vacation package. Check the “Package” heading, then select your travel dates and destination to browse some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Oak Park?
If you’re considering a spontaneous Oak Park getaway, check out our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
How to plan a trip to Oak Park?

  1. Choose the right time to travel: Your schedule, favorite season and the type of weather you enjoy can all influence your decision on when to visit Oak Park.
  2. Set your budget: Consider costs such as food, flights and transportation when working out how much to save for your trip to Oak Park. Then, select a property that works with your budget, whether that’s a low-cost stay or a swankier retreat.
  3. Decide how long to go away for: Now that you know more about Oak Park, you can figure out the ideal length of your break. Create a rough itinerary and allocate enough time for all the things you want to do.
  4. Combine your accommodations and airfare: After you’ve settled on your dates and duration, lock in the right Oak Park vacation package for you.

Discover the most popular places to visit in Oak Park

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

4.5/5(158 reviews)

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

Wrigley Field
McCormick Place

McCormick Place

4.5/5(141 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
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

4.5/5(19 reviews)

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.

Michigan Avenue

What to do in Oak Park

Flyover in Chicago

Flyover in Chicago

CA $55
per adult
96% of travellers recommend
Flyover in Chicago
River tour boat in Chicago

Architecture River Tour

CA $70
per adult
94% of travellers recommend
Architecture River Tour
Chicago: Willis Tower Skydeck and The Ledge Ticket

Chicago: Willis Tower Skydeck and The Ledge Ticket

CA $64
per adult
86% of travellers recommend
Chicago: Willis Tower Skydeck and The Ledge Ticket
See all activities in Oak Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.