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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
per person
Oct 17 - Oct 21
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.4/10 Very Good! (1,381 reviews)
This property was great! clean and friendly staff, walkable dinning and shopping options and a great part of town. the only downfall was the $30 per day hotel fee

Reviewed on Jul. 28, 2025

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,122 reviews)
I loved how smooth the check in process was and all the amenities. Great rooms.

Reviewed on Aug. 1, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Sep 19 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,635 reviews)
Great stay :) Mr 47 didn’t disappoint

Reviewed on Aug. 1, 2025

The Wade

The Wade

4.5 out of 5
Downtown Chicago
per person
Oct 5 - Oct 11
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (1,066 reviews)
Property is great and very nice location. Beautiful views of lakefront. Only downside is coffee service ends at 10. You can ask for a coffee maker for room but not the same.

Reviewed on Aug. 2, 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
per person
Sep 19 - Sep 22
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

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Midlothian Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from Sep 1 to Sep 2
CA $185
CA $217 total
Sep 1 - Sep 2
includes taxes & fees
7.8/10 Good! (8,940 reviews)
"Very convenient location. Easy check-in, even with a very crowded lobby. Polite staff."

Reviewed on Aug. 1, 2025

Congress Plaza Hotel
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
505 N Michigan Ave, Chicago, IL
Fully refundable
The price is CA $281 per night from Sep 1 to Sep 2
CA $281
CA $374 total
Sep 1 - Sep 2
includes taxes & fees
9/10 Wonderful! (2,150 reviews)
"Loved this hotel. We had a king classic in grand tower high floor. Our bed was comfy, shower was nice, room was large enough and loved the colors. View was decent. Bar had great drinks. Pool is gorgeous. The only negative was the elevators which were compact and wait times were very long sometimes. ..."

Reviewed on Aug. 1, 2025

InterContinental Chicago Magnificent Mile by IHG
Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is CA $201 per night from Aug 24 to Aug 25
CA $201
CA $236 total
Aug 24 - Aug 25
includes taxes & fees
8.8/10 Excellent! (1,324 reviews)
"It is renovated, it is very clean, the breakfast was delicious"

Reviewed on Jul. 30, 2025

Crowne Plaza Chicago West Loop by IHG
See all 3,105 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Discover the most popular places to visit in Midlothian

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
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
Navy Pier

Navy Pier

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

Navy Pier

What to do in Midlothian

River tour boat in Chicago

Architecture River Tour

CA $57
per adult
96% of travellers recommend
Architecture River Tour
Couple on a sightseeing boat in Chicago

Skyline Lake Tour

CA $41
per adult
92% of travellers recommend
Skyline Lake Tour
Skyline Queen showcasing the Chicago Skyline!

Chicago Sightseeing River and Lake Cruise

CA $62
per adult
100% of travellers recommend
Chicago Sightseeing River and Lake Cruise
See all activities in Midlothian

Frequently asked questions

How much does a Midlothian vacation package cost?
You'll find cheap prices from CA $862 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.

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