Lincolnshire Vacation Packages

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    Save up to CA $4,200 when you book a flight and hotel together*
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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.
The Talbott, Autograph Collection

The Talbott, Autograph Collection

Downtown Chicago
CA $872
per person
Nov 20 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (179 reviews)
Close to every things, great location

Reviewed on Oct 16, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

Downtown Chicago
Save 100% on your flight
CA $1,759
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,002 reviews)
Timber Ridge Lodge and Waterpark

Timber Ridge Lodge and Waterpark

CA $1,565
per person
Dec 20 - Dec 27
found 9 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
8.6/10 Excellent! (3,460 reviews)
Level Chicago Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,198
per person
Nov 16 - Nov 19
found 13 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.2/10 Wonderful! (576 reviews)
Swissotel - Chicago

Swissotel - Chicago

Downtown Chicago
CA $1,029
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,523 reviews)
Everyone was so nice and accommodating. The location is great. We had a great view of the river.

Reviewed on Oct 15, 2026

Ready to book your vacation to Lincolnshire?

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Lincolnshire Hotel Deals

Courtyard by Marriott Chicago Lincolnshire

Courtyard by Marriott Chicago Lincolnshire

505 Milwaukee Ave Lincolnshire IL
Fully refundableReserve now, pay when you stay
CA $180
CA $201 total
Oct 23 - Oct 24
includes taxes & fees
Courtyard by Marriott Chicago Lincolnshire
Hilton Chicago O'Hare Airport

Hilton Chicago O'Hare Airport

O'Hare International Airport Chicago IL
Fully refundableReserve now, pay when you stay
CA $306
CA $360 total
Nov 13 - Nov 14
includes taxes & fees
Hilton Chicago O'Hare Airport
Marriott Chicago O'Hare

Marriott Chicago O'Hare

8535 West Higgins Road Chicago IL
Fully refundableReserve now, pay when you stay
CA $229
CA $268 total
Oct 30 - Oct 31
includes taxes & fees
Marriott Chicago O'Hare
See all 1,626 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.

Stay near popular Lincolnshire attractions

Marriott Theatre

9.0/10 (48 reviews)
You can make plans for a show at Marriott Theatre during your stay in Lincolnshire. Stroll along the lakeside or attend a sporting event in the area.
See properties

Maze

Enjoy an outing to Maze during your stay in Lincolnshire. While in this family-friendly area, you can savor the top-notch restaurants.
See properties

What to do in Lincolnshire

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $59
per adult
88% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $63
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Lincolnshire

Frequently asked questions

How much does a Lincolnshire vacation package cost?
Offering excellent value package deals from CA $872 on Expedia, you'll be thrilled with how little a vacation to Lincolnshire costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Lincolnshire?
If you'd like to score a cheap Lincolnshire vacation package, consider travelling in January, February and November. You'll usually find better prices on airfares and hotels during these months — perfect for a budget-friendly getaway.
How many days is enough for Lincolnshire?
To get the most out of a Lincolnshire vacation, we suggest staying for 3 days. Split your time between discovering Chevy Chase Country Club, Heritage Park and other must-see attractions, in addition to experiencing neighbourhoods like Riverwoods and Bannockburn. If you've got some spare time, add a day trip to your Lincolnshire vacation itinerary.
Is it worth booking a vacation package to Lincolnshire?
During your Lincolnshire vacation, you can look forward to experiencing some top-notch golfing and nature. Leave enough room in your schedule to discover major sights like Marriott Theatre and Par-King Skill Golf.
How to find the best Lincolnshire package deals?
Finding a cheap Lincolnshire package deal is a cinch with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, add some filters and see what's available. You can customize your search by "Area," "Amenities," "Property type" and more. Order the results by "Price: low to high" to view the most pocket-friendly Lincolnshire package deals. Want a simple trick to score the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Lincolnshire vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging accommodations and flights separately. Better still, you can customize your Lincolnshire trip to fit your exact needs. Pick your preferred flight time, select the hotel type and add a car rental. Browse our great deals to see how much you can save.
When to book a vacation package to Lincolnshire?
Score incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your style, grab one of our last-minute deals for an impromptu Lincolnshire break.
How to plan a trip to Lincolnshire?
  1. Pick the best time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to visit Lincolnshire.
  2. Budget wisely: As well as the price of your accommodations, you should factor in other expenses. These include food, transportation and flights. Also, put aside some extra funds for unexpected expenses that could crop up during your trip to Lincolnshire.
  3. Decide how long to go away for: Now that you're more familiar with Lincolnshire, you can work out the perfect length of your break. Pull together a draft itinerary and give yourself enough time to get through everything on your must-do list.
  4. Combine your airfare and accommodations: Once you've nailed down your dates and duration, lock in the perfect Lincolnshire vacation package for you.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.