Lincolnshire Vacation Packages

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Your Lincolnshire Vacation

With everything planned before you head off, our Lincolnshire vacation packages mean you can concentrate on having a good time. Whether you base yourself in the neighborhood of Riverwoods, which is good for nature, or someplace else, this exciting city offers plenty of discoveries. Want to get out and explore? Lake Forest College, Marriott Theatre and Kemper Lakes Golf Club are among the most popular places to visit during your trip to Lincolnshire. Whatever your travel plans or budget, organizing a tailored Lincolnshire vacation is simple with Expedia.

Top Lincolnshire Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $1,548, price is now CA $1,043 per person
CA $1,043
per person
Jul 1 - Jul 5
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (480 reviews)
Room was not cleaned/ towels weren't replaced for the duration of our 3 night stay which I found rather peculiar. They also only provided 1 key for our room. I had believed it was common practice to provide 2. Other than that, the room was clean when we arrived, the bedding was comfortable, and the gym was lovely.

Reviewed on May 22, 2026

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $2,231, price is now CA $1,411 per person
CA $1,411
per person
Aug 2 - Aug 7
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (474 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.

Reviewed on May 18, 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 $3,275, price is now CA $2,074 per person
CA $2,074
per person
Jul 31 - Aug 5
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
Walls are paper thin. We literally heard snoring all night from the room next to us. Also, the smell of cigarette smoke kept coming into our room. Rooms were nice and clean. The view was 🔥.

Reviewed on May 23, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was CA $2,988, price is now CA $1,971 per person
CA $1,971
per person
Jul 31 - Aug 5
found 6 hours ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,727 reviews)
Very comfortable stay.

Reviewed on May 24, 2026

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Price was CA $1,769, price is now CA $1,257 per person
CA $1,257
per person
Aug 10 - Aug 15
found 1 hour ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9/10 Wonderful! (1,006 reviews)
Great place to stay and excellent breakfast choices

Reviewed on May 14, 2026

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Lincolnshire 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 $329 per night from Jun 19 to Jun 20
CA $329
CA $386 total
Jun 19 - Jun 20
includes taxes & fees
8.4/10 Very Good! (2,304 reviews)
"Good fitness facility , dated room, charged us extra $50 to check in before 3 pm but we were so tired after 14+ hr flt we did. Just picked the hotel bc of proximity to airport"

Reviewed on May 24, 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 $234 per night from May 26 to May 27
CA $234
CA $266 total
May 26 - May 27
includes taxes & fees
8.8/10 Excellent! (2,568 reviews)
"Breakfast and food was very expensive Staff was extremely nice Room is very clean bathroom a bit tiny"

Reviewed on May 24, 2026

Hyatt Regency O'Hare Chicago
Holiday Inn Chicago O'Hare – Rosemont by IHG

Holiday Inn Chicago O'Hare – Rosemont by IHG

3 out of 5
6600 Mannheim Road, building 2 Rosemont IL
Fully refundable
The price is CA $187 per night from Jun 21 to Jun 22
CA $187
CA $215 total
Jun 21 - Jun 22
includes taxes & fees
9/10 Wonderful! (2,962 reviews)
"."

Reviewed on May 23, 2026

Holiday Inn Chicago O'Hare – Rosemont by IHG
See all 1,673 properties in Lincolnshire
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
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Family Vacations

Discover the most popular places to visit in Lincolnshire

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 Lincolnshire

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Flyover in Chicago

Flyover in Chicago

CA $31
per child
98% of travellers recommend
Flyover in Chicago
See all activities in Lincolnshire

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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.