Midlothian Vacation Packages
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Your Midlothian Vacation
When a break in the city is calling, answer it with a vacation package to Midlothian. The neighborhood of Woodlawn, which is great for cycling, golfing and walking, makes a fantastic base for your adventures. Fill your itinerary with visits to Coyote Run Golf Course, Ravisloe Country Club and Veterans Memorial Park, some of the attractions you shouldn't miss during a trip to Midlothian. Whatever your travel plans or budget, organizing a tailored Midlothian vacation is a breeze with Expedia.
Top Midlothian Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
CA $1,805
per person
Nov 19 - Nov 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (2,035 reviews)
Free upgrade was amazing and staff were even better. Thank you.
Reviewed on Oct 6, 2026
Ready to book your vacation to Midlothian?
Midlothian Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $165
CA $196 total
Nov 2 - Nov 3
includes taxes & fees
8/10 Very good! (10,201 reviews)
"The hotel is very old so if you want something modern this is not where to go. The elevators are very slow and old better to take the stairs but the carpets are all broken. For the price I would have expected a bigger room and bathroom."
Reviewed on Oct 7, 2026
River Hotel
75 East Wacker Drive Chicago IL
CA $237
CA $282 total
Nov 1 - Nov 2
includes taxes & fees
8.8/10 Excellent! (5,504 reviews)
"Clean and very helpful staff. Great location!"
Reviewed on Oct 7, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
CA $194
CA $231 total
Nov 1 - Nov 2
includes taxes & fees
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.
What to do in Midlothian
Skydeck Chicago at Willis Tower
CA $59
per adult
88% of travellers recommend
Wendella's Lake and River Architecture Tour
CA $63
per adult
94% of travellers recommend
Frequently asked questions
How much does a Midlothian vacation package cost?
You'll find cheap prices from CA $870 on Expedia for your Midlothian escape. However, factors like the season, length of stay and your choice of hotel will influence how much your vacation to Midlothian costs.
What are the cheapest months to go to Midlothian?
January, February and November are great times to search for cheap Midlothian vacation packages. Choosing to travel in less busy months means you can typically find better prices on flights and accommodations.
How many days is enough for Midlothian?
We recommend planning a Midlothian vacation for a minimum of 2 days. This will allow you time to tick off major attractions including Hollywood Park and Midwest Carvers Museum, and check out neighbourhoods like East Hazel Crest and Country Club Hills. You could even make time for a day trip (or two) outside of Midlothian.
How to find the best Midlothian package deals?
Landing a cheap Midlothian package deal is a breeze with Expedia. Once you've entered your destination and trip dates under our "Packages" tab, set your maximum budget, add a few filters and browse what's available. You can personalize your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most affordable Midlothian package deals. Want a simple trick to score the biggest savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are typically lower.
Is it cheaper to book a Midlothian vacation as a package?
You can enjoy significant savings on your next Midlothian escape by booking a customized vacation package. Check the "Package" heading, then enter your travel dates and destination to browse the best airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a vacation package to Midlothian?
If you're considering a spontaneous Midlothian adventure, browse our last-minute deals that can be booked up to a week before you go. Prefer not to wait until the last minute? You can score awesome deals on your flights and hotels by booking ahead.
How to plan a trip to Midlothian?
- Choose when to go: Check your calendar and pack your bags. Your preferred time of year and the available activities will also help you decide when to visit Midlothian.
- Plan your budget wisely: As well as the cost of your accommodations, you should factor in other expenses too. These include food, flights and transportation. Also, put aside some extra funds for unexpected costs that could arise during your trip to Midlothian.
- Decide how many days away: Start by making a list of all the attractions and activities you want to get to in Midlothian. Then, estimate how long you'll need at each, along with any travel time.
- Bundle your bookings: With your travel dates in order, you can combine your flights, hotels, car rental and more into a tailored Midlothian vacation package.
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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.
