Midlothian Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

Photo by Erik Rowley
  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*
  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • Rest easy

    Plan, book, and manage your trip all in one place

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 Fulton Market

Level Chicago Fulton Market

Downtown Chicago
CA $1,361
per person
Nov 15 - Nov 21
found 16 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (556 reviews)
Great! But parking was bad.

Reviewed on Aug 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

Downtown Chicago
CA $1,615
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,986 reviews)
隔音效果差

Reviewed on Aug 27, 2026

The Emily Hotel

The Emily Hotel

Downtown Chicago
CA $1,539
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (1,339 reviews)
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

Downtown Chicago
CA $1,727
per person
Oct 9 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (5,045 reviews)
Level Chicago – Old Town

Level Chicago – Old Town

Downtown Chicago
CA $1,555
per person
Oct 18 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Chicago (ORD)
9.2/10 Wonderful! (520 reviews)

Ready to book your vacation to Midlothian?

Choose your dates

Midlothian Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
CA $148
CA $176 total
Sep 8 - Sep 9
includes taxes & fees
8/10 Very good! (10,201 reviews)
"Second time staying here. Love how close is to stores, walkable everywhere."

Reviewed on Aug 29, 2026

Congress Plaza Hotel
Kasa Magnificent Mile Chicago

Kasa Magnificent Mile Chicago

One Superior Place Chicago IL
9.4/10 Exceptional! (878 reviews)
"We enjoyed our experience. It was clean and quiet and in the heart of the city. A true gem. I cannot wait to return!"

Reviewed on Aug 29, 2026

Get rates
Kasa Magnificent Mile Chicago
Hyatt Regency McCormick Place Chicago

Hyatt Regency McCormick Place Chicago

2233 S Martin Luther King Dr Chicago IL
Fully refundableReserve now, pay when you stay
CA $291
CA $386 total
Aug 30 - Aug 31
includes taxes & fees
Hyatt Regency McCormick Place Chicago
See all 3,061 properties in Midlothian
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

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

CA $34
per adult
90% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $62
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
See all activities in Midlothian

Frequently asked questions

How much does a Midlothian vacation package cost?
You'll find cheap prices from CA $1,361 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?
  1. 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.
  2. 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.
  3. 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.
  4. 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.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.