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.
HYATT house Chicago/Schaumburg

HYATT house Chicago/Schaumburg

3.5 out of 5
per person
Sep 11 - Sep 15
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Chicago (ORD)
7.8/10 Good! (1,003 reviews)
Nice hotel in a nice area

Reviewed on Aug. 5, 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.4/10 Exceptional! (1,679 reviews)
Amazing property well worth the money

Reviewed on Aug. 11, 2025

The Royal Sonesta Chicago River North

The Royal Sonesta Chicago River North

4.5 out of 5
Downtown Chicago
per person
Oct 16 - Oct 19
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Chicago (ORD)
9.2/10 Wonderful! (1,980 reviews)
Doorman was delightful! King room was spacious. Toilet flush was problematic. The pool was not open despite the advertisement on the Expedia websit. Lots of additional, non-negotiable charges once you get there.

Reviewed on Aug. 11, 2025

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
per person
Oct 24 - Oct 28
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,159 reviews)
We really enjoyed our stay at The Emily Hotel. We had a great room at a great price. The check in was quick and easy, we valeted our car which was worth every penny for the convenience. Coffee every morning and a cocktail every evening at the hotel were very nice. The area around the hotel is a whirlwind of fantastic dining and nightlife options. If you're looking for upscale fun for the weekend, you'll love The Emily Hotel in Chicago!

Reviewed on Aug. 12, 2025

Hilton Orrington / Evanston

Hilton Orrington / Evanston

4 out of 5
Downtown Evanston
per person
Oct 30 - Nov 2
found 1 day ago
Roundtrip flight included
Montreal (YUL) to Chicago (ORD)
7.6/10 Good! (1,003 reviews)
This property was right in the heart of downtown and right next to Northwestern - it's a perfect location, and was clean and comfortable!

Reviewed on Aug. 11, 2025

Ready to book your vacation to Midlothian?

 

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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! (8,958 reviews)
"Super convenient to everything we needed or wanted Hotel is good, location is great"

Reviewed on Aug. 11, 2025

Congress Plaza Hotel
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $239 per night from Aug 21 to Aug 22
CA $239
CA $315 total
Aug 21 - Aug 22
includes taxes & fees
8.4/10 Very Good! (1,848 reviews)
"5 star rating! The vibe of the hotel is amazing and you can’t beat the location."

Reviewed on Aug. 11, 2025

Palmer House a Hilton Hotel
Hilton Garden Inn Chicago Downtown/Magnificent Mile

Hilton Garden Inn Chicago Downtown/Magnificent Mile

3 out of 5
10 E Grand Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is CA $217 per night from Aug 26 to Aug 27
CA $217
CA $254 total
Aug 26 - Aug 27
includes taxes & fees
8.4/10 Very Good! (3,648 reviews)
"Good"

Reviewed on Aug. 10, 2025

Hilton Garden Inn Chicago Downtown/Magnificent Mile
See all 3,182 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

4.5/5(158 reviews)

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

4.5/5(19 reviews)

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

4.5/5(459 reviews)

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
See Chicago's magnificent skyline at night!

Chicago By Night River & Lake Cruise

CA $62
per adult
96% of travellers recommend
Chicago By Night River & Lake Cruise
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $56
per adult
94% of travellers recommend
Wendella's 90-min Chicago 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 $460 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.