
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.

Omni Chicago Hotel
Downtown Chicago
Price was CA $784, price is now CA $605 per person
CA $605
per person
Aug 11 - Aug 13
found 23 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.2/10 Wonderful! (1,819 reviews)
Great location and a friendly staff made this a great experience. The rooms are very nice, but a little dated, which made it feel a little less clean. The staff was amazing, especially the doorman/bellman, Ham. He went out of his way help everytime we arrived or departed, he asked how our day was and offered directions. I really can’t speak highly enough of him. We didn’t utilize the restaurant while there, but I did visit the bar and they had an excellent selection of high end bourbons.
Reviewed on Jul 11, 2026

Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,101, price is now CA $778 per person
CA $778
per person
Sep 5 - Sep 8
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very good! (2,809 reviews)
The good:
Staff was great
Location
Comfortable bed
The bad:
Extra daily charge that you are told about as you check in. I'm sure it's in the fine print but I saw nothing special that extra cost (6 nights it added up) got the guests and I think that's a real insult when we already paying a lot of $$.
Water pressure and heat of water terrible.
TV didn't work very well
Not much in room - small, no fridge, no microwave
I'd stay again in a pinch but will avoid - especially because of the inexplicable daily fee.
Reviewed on Jul 11, 2026

Level Chicago – Old Town
Downtown Chicago
Price was CA $3,029, price is now CA $2,213 per person
CA $2,213
per person
Sep 21 - Sep 28
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9/10 Wonderful! (497 reviews)
We traveled with four kids. There was a noticeable lack of other children around. However the property was prepared to have them around. There was an entire play room with brand new puzzles and gently used toys to play with. The pool was usually fairly empty so my kids had fun there. The basketball court was generally empty as well. We got a lot of use out of all three spaces. The staff was friendly and helpful. And the coffee shop downstairs was a frequent stop as well.
Reviewed on Jul 9, 2026

Nobu Hotel Chicago
Downtown Chicago
Price was CA $1,264, price is now CA $977 per person
CA $977
per person
Aug 18 - Aug 20
found 23 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.4/10 Exceptional! (879 reviews)
Stunning hotel with really attentive staff, located in the heart of Chicago's West Loop neighborhood. You are surrounded by a ton of award-winning restaurants, shopping and also close to public transit. Rooms are spacious and are themed in a minimalistic Japanese onsen-style esthetic. We loved our stay here, though there are a few things to mention that made our stay less than a perfect 10. The bathroom is fully painted in black. Looks great, but terrible for styling your hair, if you have dark colored hair. Poor lighting concepts throughout the room and bathroom in general, which made it terrible for getting ready any time of the day. Closet area was dark, not great for getting dressed. Bedroom area was dark, not great for reading a book. Desk area is dark, not great for working remotely. Bathroom lighting is dark, not great if you are a woman trying to put on makeup. Housekeeping was fantastic and really knew how to personalize your stay, but they still knocked on the door when we had the "do not disturb" light on, which was very bothersome and woke us up a couple of times.
Reviewed on Jul 6, 2026

Level Chicago - River North
Downtown Chicago
Price was CA $974, price is now CA $753 per person
CA $753
per person
Aug 11 - Aug 13
found 23 hours ago
Roundtrip non-stop flight included
Buffalo (BUF) to Chicago (ORD)
9.2/10 Wonderful! (1,020 reviews)
Amazing and beautiful hotel with caring and helpful staff!
Reviewed on Jul 8, 2026
Oak Park Hotel Deals

The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $218 per night from Jul 27 to Jul 28
CA $218
CA $259 total
Jul 27 - Jul 28
includes taxes & fees
8.2/10 Very good! (1,734 reviews)
"Surprise fees upfront when you book with third party sites like, Expedia. Expect to cough up a few hundred dollars before you even get to the elevator. Other than that it’s a gorgeous hotel with incredible surrounding areas. Not too far from the beach as well. The breakfast buffet was also ..."
Reviewed on Jul 11, 2026

Omni Chicago Hotel
676 N Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $316 per night from Jul 26 to Jul 27
CA $316
CA $422 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (1,908 reviews)
"Great location and a friendly staff made this a great experience. The rooms are very nice, but a little dated, which made it feel a little less clean. The staff was amazing, especially the doorman/bellman, Ham. He went out of his way help everytime we arrived or departed, he asked how our day was ..."
Reviewed on Jul 11, 2026

Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $268 per night from Aug 10 to Aug 11
CA $268
CA $318 total
Aug 10 - Aug 11
includes taxes & fees
8/10 Very good! (10,229 reviews)
"Older hotel, but nice"
Reviewed on Jul 11, 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.
What to do in Oak Park

Chicago: Navy Pier Centennial Wheel Ticket
CA $35
per adult
88% of travellers recommend

Wendella's Lake and River Architecture Tour
CA $64
per adult
94% of travellers recommend
Frequently asked questions
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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.













