Lake Forest Vacation Packages

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Your Lake Forest Vacation

Put together a custom vacation package to Lake Forest and prepare to experience this incredible city on your own terms. Think about spending some time in the neighborhood of Riverwoods, which is good for nature and lots more. Every trip to Lake Forest needs a well-crafted itinerary. Fill yours with big-name attractions like Lake Forest College, Marriott Theatre and Trinity International University. No matter your travel plans or the size of your budget, organizing a tailored Lake Forest vacation is a piece of cake with Expedia.

Top Lake Forest Vacation Deals

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

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,443, price is now CA $1,038 per person
CA $1,038
per person
Aug 6 - Aug 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,124 reviews)
Great staff and perfect place to be in the middle of everything!

Reviewed on Apr 27, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,632, price is now CA $1,645 per person
CA $1,645
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
we didn't have breakfast at the hotel

Reviewed on May 11, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,921, price is now CA $1,279 per person
CA $1,279
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,155, price is now CA $1,480 per person
CA $1,480
per person
Jul 13 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.

Reviewed on May 8, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was CA $2,384, price is now CA $1,717 per person
CA $1,717
per person
Jul 30 - Aug 2
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Horrible, horrible housekeeping staff many times I had to have head of housekeeping come and monitor Very disappointing

Reviewed on May 10, 2026

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Lake Forest Hotel Deals

Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

4 out of 5
O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $347 per night from May 24 to May 25
CA $347
CA $408 total
May 24 - May 25
includes taxes & fees
8.4/10 Very Good! (2,290 reviews)
Trainee staff was really trying to get it right. Trainer was very good.

Reviewed on May 10, 2026

Hilton Chicago O'Hare Airport
Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

4 out of 5
9300 Bryn Mawr Ave Rosemont IL
Fully refundableReserve now, pay when you stay
The price is CA $231 per night from May 21 to May 22
CA $231
CA $263 total
May 21 - May 22
includes taxes & fees
8.8/10 Excellent! (2,550 reviews)
The staff were kind and helpful, everything was clean, and I appreciated the free shuttle to/from O'Hare (and that it was close to the airport). I think having a proper little shop for travelers' needs, rather than a faulty vending machine, would make it just a wee bit better, but overall the experience ...

Reviewed on May 11, 2026

Hyatt Regency O'Hare Chicago
Marriott Chicago O'Hare

Marriott Chicago O'Hare

3.5 out of 5
8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $208 per night from May 25 to May 26
CA $208
CA $244 total
May 25 - May 26
includes taxes & fees
8.6/10 Excellent! (1,248 reviews)
Check in took a bit longer than expected which seemed to be due to staffing issues. The room was clean and ready for us upon check in. The parking available through the hotel and also the long-term airport parking were a bit confusing for our stay and we left for our trip still unsure of if we were ...

Reviewed on May 4, 2026

Marriott Chicago O'Hare
See all 1,582 properties in Lake Forest
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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Discover the most popular places to visit in Lake Forest

Wrigley Field

Wrigley Field

4.5/5(159 reviews)

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

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(460 reviews)

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

Navy Pier

What to do in Lake Forest

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
94% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $61
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
See all activities in Lake Forest

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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.