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.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,000 reviews)
Our room was nice. The hotel concierge staff was attentive. Maid service was subpar. We repeatedly asked for replacement items and only half were fulfilled. Great central location, but unsure if we will return because of lacking maid service.

Reviewed on Jul. 24, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 10 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
The room was excellent and clean! And such a great location!

Reviewed on Jul. 23, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Accessibility to Wendella Tours, shopping and the ‘L’ to go sightseeing

Reviewed on Jul. 24, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Aug 29 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,000 reviews)
It's a beautiful and comfortable hotel.

Reviewed on Jul. 22, 2025

Hilton Garden Inn Chicago Downtown South Loop

Hilton Garden Inn Chicago Downtown South Loop

3 out of 5
Downtown Chicago
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,584 reviews)
FLIES!! Dining in the restaurant near the kitchen, getting carpet-bombed by a battalion of flies. Distracted while eating in restaurant with guest. Swarmed the next day while checking out. Staff oblivious. Said they “would” report, instead of they “HAD” reported.

Reviewed on Jul. 23, 2025

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Lincolnshire Hotel Deals

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 $195 per night from Jul 27 to Jul 28
CA $195
CA $223 total
Jul 27 - Jul 28
includes taxes & fees
8.6/10 Excellent! (1,772 reviews)
"Awesome experience"

Reviewed on Jul. 22, 2025

Hyatt Regency O'Hare Chicago
Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG

3.5 out of 5
5440 N River Rd, Rosemont, IL
Fully refundable
The price is CA $178 per night from Aug 10 to Aug 11
CA $178
CA $203 total
Aug 10 - Aug 11
includes taxes & fees
8.6/10 Excellent! (2,316 reviews)
"Our stay at the Crowne Plaza Rosemont was nice. It was a business trip for a conference. The elevators had some issues and with so many people in for the conference it made it a bit of a “log jam” at times. The staff was very friendly. The location was perfect with several restaurants within walking ..."

Reviewed on Jul. 20, 2025

Crowne Plaza Chicago Ohare Hotel & Conf Ctr by IHG
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 $244 per night from Aug 23 to Aug 24
CA $244
CA $286 total
Aug 23 - Aug 24
includes taxes & fees
8/10 Very Good! (2,072 reviews)
"Overall a great hotel for my needs. Had my flight come in late at night and next segment early in am."

Reviewed on Jul. 23, 2025

Hilton Chicago O'Hare Airport
See all 1,554 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
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Discover the most popular places to visit in Lincolnshire

Wrigley Field featuring central business district, a city and a sporting event

Wrigley Field

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

Wrigley Field
Navy Pier

Navy Pier

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

Navy Pier
Magnificent Mile - River North which includes signage, a city and night scenes

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue

What to do in Lincolnshire

River tour boat in Chicago

Architecture River Tour

CA $67
per adult
96% of travellers recommend
Architecture River Tour
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
See all activities in Lincolnshire

Frequently asked questions

How much does a Lincolnshire vacation package cost?
Offering excellent value package deals from CA $912 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.