
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
Downtown Chicago
Price was CA $898, price is now CA $645 per person
CA $645
per person
Jul 19 - Jul 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,378 reviews)
The location was amazing though the rooms were a bit run down.
Reviewed on Jun 18, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,935, price is now CA $1,281 per person
CA $1,281
per person
Jul 22 - Jul 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,779 reviews)
The front foyer had beautiful glass bulbs that were very dusty and dirty. Not a good first impression
Housekeeping or room service could have been disclosed for 4 nights garbage build up Also notice we had no bathroom hooks to hang wet towels just one towel bar.
Bed was comfortable and linens were fine.
Oh and, $8 bottle of Voss water in room no cups in room or bathroom. Microwave breakfast 😑
Reviewed on Jun 15, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $1,999, price is now CA $1,337 per person
CA $1,337
per person
Sep 2 - Sep 6
found 9 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (489 reviews)
We love where this is property is located and all the amenities. The pool was closed the 2 days we were there which was disappointing but the weather didn't really cooperate either. The staff is very accomodating and attentive.
Reviewed on Jun 11, 2026

Hampton Inn & Suites Chicago Medical District UIC
Near West Side
Price was CA $1,450, price is now CA $1,067 per person
CA $1,067
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.6/10 Exceptional! (622 reviews)
The location is perfect. The staff was friendly, parking was easy, really clean, modern and had everything you needed in a room. I really enjoyed this room with my 16- year old daughter for her birthday. We had a connecting room for her and her friends which was perfect as a patient. I was able to keep my ear to the door and my eyes to the food court where the group enjoyed the grass and space and water fountain out front. It was perfect for a 16th Birthday celebration
Reviewed on Jun 16, 2026

The Emily Hotel
Downtown Chicago
Price was CA $958, price is now CA $721 per person
CA $721
per person
Sep 12 - Sep 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,327 reviews)
The staff was great. The room was nice but I would have preferred more towels. The remote in our room wasn’t working fully as well as the steamer in the room. Otherwise, it is a good hotel but would not recommend for families.
Reviewed on Jun 15, 2026
Oak Park Hotel Deals

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $192 per night from Jun 29 to Jun 30
CA $192
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,297 reviews)
"We were very pleased with our stay at Congress Plaza Hotel. Location was perfect for sightseeing. Many restaurant choices within walking distance. Our room had a beautiful view of Buckingham Fountain and Lake Michigan. Staff was friendly and helpful. Would definitely stay here again."
Reviewed on Jun 18, 2026

The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $223 per night from Jul 5 to Jul 6
CA $223
CA $266 total
Jul 5 - Jul 6
includes taxes & fees
7.8/10 Good! (1,589 reviews)
"Beautiful room, clean, nice staff"
Reviewed on Jun 18, 2026

Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jul 2 to Jul 3
CA $203
CA $231 total
Jul 2 - Jul 3
includes taxes & fees
8.8/10 Excellent! (2,688 reviews)
"Hotel main trash service pickup was directly below my room window and was extremely loud when unloading and loading rolloff dumpsters at 4am. No way to sleep through the noise. Shuttle service was very good to and from the airport. Toilet clogged after one use with no plunger available. Remodeling ..."
Reviewed on Jun 17, 2026
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.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.












