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.
Level Chicago - River North
Downtown Chicago
CA $1,387
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,043 reviews)
The hotel had everything we needed. I do think it could be a super cold place to try to sleep in the winter with all the glass walls. It was cold at night even in August. It was also incredibly loud all throughout the night. I was glad I thought to bring a few warm layers and earplugs. The people working at the front desk and around the hotel were all super friendly and welcoming.
Reviewed on Aug 22, 2026
Four Seasons Hotel Chicago
Downtown Chicago
CA $2,256
per person
Oct 11 - Oct 14
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Stayed for a weekend trip. Staff were extremely attentive and knowledgeable about the property and city in general. Room arrangement and amenities were excellent. Pool was larger than expected for a ‘high rise’ pool, and very family friendly - towels/locker room was well stocked. Location in relation to city is perfect for shopping and local excursions, but would recommend uber/lift to get around
Reviewed on Aug 16, 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 $142
CA $169 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,283 reviews)
"Do not stay at this hotel! It’s very outdated and looks like an old Catholic college dorm. It’s not worth the money and you’re only paying for the location. Normally hotels have valet parking if you plan to do parking . Not this hotel! You have to drive yourself and the parking structure doesn’t ..."
Reviewed on Aug 22, 2026
Kasa Magnificent Mile Chicago
One Superior Place Chicago IL
9.4/10 Exceptional! (865 reviews)
"Awesome stay. I love the property. Staff comfort me when I found out that my dad passed away. This is/was going beyond the call of duty and doing an extra great job so 10 stars. You are greatly appreciated. Primetime location downtown near magnificent mile and Navy Pier,"
Reviewed on Aug 21, 2026
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
CA $268
CA $359 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (1,295 reviews)
"Overall, the hotel was not bad. However, during check-in, I was not given clear information about additional charges, such as the cost for parking. Also, after departing, I realized I had forgotten an item and called as soon as I remembered, but I was told the item was not there."
Reviewed on Aug 22, 2026
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
Chicago: Navy Pier Centennial Wheel Ticket
CA $34
per adult
90% 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 $1,387 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.
