Highland Park Vacation Packages
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Your Highland Park Vacation
Planning your next big adventure is a piece of cake with a Highland Park vacation package. The neighborhood of Riverwoods, which is great for nature, makes a superb base to uncover the marvels of this unique city. If sightseeing is part of the plan during your trip to Highland Park, check out well-known attractions like Chicago Botanic Garden, Lake Forest College and Northbrook Sports Complex. Whoever you're escaping with and whatever you plan to spend, your dream Highland Park vacation is just clicks away with Expedia.
Top Highland Park Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Gurnee
Price was CA $915, price is now CA $688 per person
CA $688
per person
Jun 18 - Jun 23
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Chicago (ORD)
7.8/10 Good! (1,004 reviews)
The room was very clean and comfortable. Breakfast was also your normal hotel breakfast. Overall the entire team of staff was phenomenal.
Reviewed on Mar 30, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,180, price is now CA $1,427 per person
CA $1,427
per person
May 31 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.4/10 Exceptional! (2,427 reviews)
Breakfast and parking not included
Reviewed on Apr 12, 2026
Sports Illustrated Resorts Chicago
Downtown Chicago
Price was CA $1,934, price is now CA $1,355 per person
CA $1,355
per person
May 31 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Great location and converted old Virgin Hotel. Room was fine and hotel basics were fine. There wasn’t any room service daily or for my 3 night stay. There was a strike for housekeepers and they were LOUD out front everyday. Not sure what the hotel fee was for on top of Expedia hotel charge was for, they gave me 2 waters the first day and that was it. They also upsell their vacation club/time share a lot, kinda odd.
Reviewed on Apr 14, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,484, price is now CA $1,060 per person
CA $1,060
per person
Jul 3 - Jul 5
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (453 reviews)
This property never disappoints! The staff are awesome, particularly Nu at the front desk! Always very pleasant and friendly, provides awesome service every time we visit!
Reviewed on Apr 13, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $2,243, price is now CA $1,680 per person
CA $1,680
per person
May 31 - Jun 3
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Chicago (ORD)
9.2/10 Wonderful! (902 reviews)
The check in process was a little crazy, can’t say I have ever needed a background check to stay somewhere so it was a bit time consuming although I suppose good to know safety is a priority. View from property was the best part hands down! Cost of overall stay was great deal, parking for $65 a night was a bit disappointing because it is nice to have it on site. Overall would stay again.
Reviewed on Apr 14, 2026
Highland Park Hotel Deals
Hilton Chicago O'Hare Airport
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $343 per night from May 9 to May 10
CA $343
CA $403 total
May 9 - May 10
includes taxes & fees
8.4/10 Very Good! (2,277 reviews)
I would rate this hotel as good to excellent if not for one employee. I stayed two nights and all the staff including front desk, restaurant and housekeeping were customer friendly and efficient with one exception. I returned back to the main entrance of the hotel on the second night after a long ...
Reviewed on Apr 12, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $153 per night from Apr 28 to Apr 29
CA $153
CA $180 total
Apr 28 - Apr 29
includes taxes & fees
8.2/10 Very Good! (1,365 reviews)
Nice place to lay your head
Reviewed on Apr 14, 2026
Hyatt Regency O'Hare Chicago
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $201 per night from Apr 23 to Apr 24
CA $201
CA $229 total
Apr 23 - Apr 24
includes taxes & fees
8.8/10 Excellent! (2,498 reviews)
The staff was not helpful. We stayed there the night before an international flight and the night we got back. We had to pay $50 per day for parking.
Reviewed on Apr 14, 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.
Discover the most popular places to visit in Highland Park
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(3 reviews)
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.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Highland Park
Skydeck - Willis Tower Admission
CA $60
per adult
98% of travellers recommend
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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.
