Midlothian Vacations from $294

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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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $1,270, price is now $294 per person
$294
per person
Dec 22 - Dec 24
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $830, price is now $507 per person
$507
per person
Dec 24 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Staff was friendly and the room was clean

Reviewed on Nov 3, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was $639, price is now $403 per person
$403
per person
Jan 5 - Jan 10
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (591 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $609, price is now $401 per person
$401
per person
Dec 16 - Dec 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)

Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $718, price is now $480 per person
$480
per person
Jan 25 - Jan 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (544 reviews)
Estuvo muy increíble, fue una experiencia maravillosa.Es un lugar precioso me encantó

Reviewed on Nov 1, 2026

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What to do in Midlothian

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

$24
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
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
Chicago's Navy Pier Centennial Wheel Ticket

Chicago's Navy Pier Centennial Wheel Ticket

$24
per adult
100% of travellers recommend
Chicago's Navy Pier Centennial Wheel Ticket
See all activities in Midlothian

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
$106 nightly
The price is $126 total per night from Nov 22 to Nov 23
$126 total
Nov 22 - Nov 23
Total with taxes and fees
Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
$110 nightly
The price is $131 total per night from Nov 26 to Nov 27
$131 total
Nov 26 - Nov 27
Total with taxes and fees
River Hotel
The Wade

The Wade

4.5 out of 5
644 N Lake Shore Dr Chicago IL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $141 total per night from Nov 23 to Nov 24
$141 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (2,185 reviews)
"Great Hotel, Amazing Views, but Some Nighttime Noise We had a wonderful stay at The Wade Hotel in Chicago! The location was excellent, the rooms were very clean and comfortable, and the views were absolutely beautiful, definitely one of the highlights of our stay. The only downside was a constant ..."

Reviewed on Nov 4, 2026

The Wade
See all 3,144 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 $294 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.

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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.