Oak Park Vacations from ￥290,255

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Oak Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥367,903, price is now ￥290,255 per person
￥290,255
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
8.2/10 Very Good! (2,582 reviews)
Great place to stay the young lady checking us in was not very friendly. Never received my complimentary drinks. There was never anyone at the bar. Valet guy was very helpful!!! Other than the small things it was a good stay!!!

Reviewed on Mar 29, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥426,090, price is now ￥293,447 per person
￥293,447
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Beautiful, amazing location, very clean, helpful staff, only negative was I was unable to purchase water after hours on site, had to make a quick walk to 7-Eleven.

Reviewed on Mar 30, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥458,800, price is now ￥362,534 per person
￥362,534
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Thank you for your exceptional hospitality

Reviewed on Mar 29, 2026

Eurostars Magnificent Mile

Eurostars Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥369,722, price is now ￥300,613 per person
￥300,613
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,314 reviews)
Room was clean, I loved that it had robes, amazing view, and couldn’t hear much noise from other rooms. One thing I will say was that it smelled humid when we arrived nothing too crazy.

Reviewed on Mar 30, 2026

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was ￥503,024, price is now ￥409,532 per person
￥409,532
per person
Jun 4 - Jun 8
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.2/10 Wonderful! (1,320 reviews)
Place was very nice.

Reviewed on Mar 26, 2026

Find the Best Oak Park Vacation Packages

Oak Park Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥18,396 per night from Apr 5 to Apr 6
￥18,396
￥21,596 total
Apr 5 - Apr 6
includes taxes & fees
8/10 Very Good! (10,015 reviews)
I don’t usually leave reviews. But this place is not it. The beds are terrible. Mattress is extremely uncomfortable and the bedding is disgusting. And despite how they word it on Expedia there is NO parking associated with this hotel.

Reviewed on Mar 30, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥21,975 per night from Apr 5 to Apr 6
￥21,975
￥25,796 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (4,020 reviews)
Great location and great service

Reviewed on Mar 30, 2026

Hilton Chicago/Magnificent Mile Suites
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 ￥22,860 per night from Apr 12 to Apr 13
￥22,860
￥26,835 total
Apr 12 - Apr 13
includes taxes & fees
8.6/10 Excellent! (5,800 reviews)
Our stay was ok. It was very crowded and we could hear the family in the room next door. Because it was crowded, you had to wait for elevators for a while. Or ride on completely packed elevators. Especially in the morning during breakfast hours. Water pressure is extremely weak in the shower. Room ...

Reviewed on Mar 30, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,969 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.

Discover the most popular places to visit in Oak Park

Wrigley Field

Wrigley Field

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

Wrigley Field
Chicago Skyline at North Beach

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

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

Navy Pier

What to do in Oak Park

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,985
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

￥3,829
per adult
88% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Art Institute of Chicago

Art Institute of Chicago

￥6,236
per adult
92% of travellers recommend
Art Institute of Chicago
See all activities in Oak Park

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.