Midlothian Vacations from $296

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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.

The Latest Midlothian vacation packages

Price found within the past 48 hours. Click for updated prices.
theWit Chicago, a Hilton Hotel

theWit Chicago, a Hilton Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $555, price is now $296 per person
$296
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,001 reviews)
My family and I stayed at The Wit for Thanksgiving and were extremely pleased with the amenities and professionalism of the staff.

Reviewed on Dec 8, 2025

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $635, price is now $355 per person
$355
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
Great location, clean room and friendly staff!

Reviewed on Dec 14, 2025

Hilton Grand Vacations Club Chicago Magnificent Mile

Hilton Grand Vacations Club Chicago Magnificent Mile

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $742, price is now $424 per person
$424
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (317 reviews)
The room was beautiful and clean and a good city view of the city

Reviewed on Nov 26, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $581, price is now $335 per person
$335
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,130 reviews)
Concierge not helpful and neither is was the door man, Neither would get me a cab, they said to just stand outside

Reviewed on Dec 4, 2025

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $541, price is now $319 per person
$319
per person
Feb 18 - Feb 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,229 reviews)
Staff was courteous and accommodating. Rooms were clean with a beautiful view.

Reviewed on Dec 16, 2025

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See all available trips from Columbus to Midlothian
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Discover the most popular places to visit in Midlothian

Magnificent Mile - River North showing night scenes, a city and signage

Michigan Avenue

4.5/5(332 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
Wrigley Field featuring cbd, a sporting event and a city

Wrigley Field

4.5/5(2,128 reviews)

Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.

Wrigley Field
Navy Pier featuring a sunset and rides

Navy Pier

4.5/5(4,870 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

$44
per adult
96% of travellers recommend
Architecture River Tour
Chicago Bulls Basketball Game at United Center

Chicago Bulls Basketball Game at United Center

$80
per adult
80% of travellers recommend
Chicago Bulls Basketball Game at United Center
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

$41
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Midlothian

Midlothian Hotel Deals

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
10 S Wabash Ave Chicago IL
Fully refundableReserve now, pay when you stay
$127 nightly
The price is $149 total per night from Jan 4 to Jan 5
$149 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.2/10 Wonderful! (2,127 reviews)
This hotel was great. In a perfect spot for walking the city and taking in all the sights. We had 3 of us in our group and we got the 1br with 2 queens beds and a pullout couch and it was perfect. The bar was fun and everyone we met in the staff were so friendly and helpful with suggestions on places ...

Reviewed on Dec 16, 2025

Silversmith Hotel Chicago Downtown
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
$133 nightly
The price is $152 total per night from Dec 30 to Dec 31
$152 total
Dec 30 - Dec 31
Total with taxes and fees
8.4/10 Very Good! (2,142 reviews)
Everything was great!

Reviewed on Dec 16, 2025

Palmer House a Hilton Hotel
Club Quarters Hotel Wacker at Michigan, Chicago

Club Quarters Hotel Wacker at Michigan, Chicago

4 out of 5
75 E Wacker Dr Chicago IL
Fully refundableReserve now, pay when you stay
$88 nightly
The price is $103 total per night from Dec 23 to Dec 24
$103 total
Dec 23 - Dec 24
Total with taxes and fees
8.6/10 Excellent! (1,992 reviews)
Great friendy staff, Smooth Check-in Check-out Process and the view from the room was just stunning.

Reviewed on Dec 16, 2025

Club Quarters Hotel Wacker at Michigan, Chicago
See all 3,167 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.

Find the Best Midlothian Vacation Packages

Midlothian Essential Information

Language
English
Currency
U.S dollars
Closest Airport
O'Hare Intl. Airport (ORD)
Population
14,800
Max Temp Winter
30ºF
Max Temp Summer
80ºF
Top Sights
Calumet Beach, Midwest Carvers Museum and Bronzeville Childrens Museum

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Frequently asked questions

How much does a Midlothian vacation package cost?
You can grab a vacation package to this destination from $296 on Expedia. But how much your vacation to Midlothian costs will depend on factors like the length of stay, season and hotel choice.
What are the cheapest months to go to Midlothian?
December, January and February are great times to look for cheap Midlothian vacation packages. Traveling in less busy periods means you can usually find better prices on hotels and flights.
How many days is enough for Midlothian?
The ideal duration of your Midlothian vacation depends on what you'd like to see and do. Generally, a few days to a week will give you enough time to tick off all the top sights and explore some hidden gems along the way.
How to find the best Midlothian package deals?
Use Expedia's filters to find some unbeatable Midlothian package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or search for Midlothian package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Midlothian vacation as a package?
You can enjoy significant savings on your Midlothian break by booking a customized vacation package. Click on the "Package" heading, then select your destination and travel dates to view the best flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Midlothian?
If you're planning an impromptu Midlothian adventure, browse our last-minute deals that can be booked up to one week before you go. Prefer not to wait until the last minute? You can land awesome deals on your flights and hotels by booking well in advance.
How to plan a trip to Midlothian?

  1. Pick your travel dates: The things you want to do in Midlothian and your favorite season will help you decide when to go.
  2. Plan your budget wisely: In addition to the cost of your stay, you should consider other expenses. These include transportation, food and flights. Also, set aside a little extra for unexpected costs that may arise during your trip to Midlothian.
  3. Use Expedia's trip planning tool to discover Midlothian: Research every part of your trip to Midlothian with this handy planner. Invite your family and friends to collaborate on a group getaway, search for stays or things to do and make bookings.
  4. Work out your trip length: Think about how much time you'd like to spend discovering Midlothian. Plan your days so you can get to all the attractions and experiences you're interested in without rushing.
  5. Bundle your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to pick a Midlothian vacation package that brings all your bookings together.
  6. Add on excursions and experiences: Take a look at our travel guide to find some incredible things to do in Midlothian in Midlothian. Book tickets or make reservations before you go to save time and skip the hassle of searching for activities when you arrive.

Does Expedia offer Book Now, Pay Later Midlothian vacation packages?
Jet off on your dream escape to Midlothian with our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until the next payday — we've partnered with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you spread the cost across 3, 6 or 12 months. With no hidden or late payment fees, it's a breeze to budget for your trip and snap up travel deals while they last.

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.