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.
Swissotel - Chicago
Downtown Chicago
Price was CA $1,297, price is now CA $867 per person
CA $867
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (3,332 reviews)
Great location and very convenient to river walk and vicinity.
Reviewed on May 22, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $2,231, price is now CA $1,411 per person
CA $1,411
per person
Aug 2 - Aug 7
found 1 hour ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (474 reviews)
Minimum effort. Pleasant stay. Very quiet. Enjoyed the 8th floor common area. Service at the front desk was really great. Convenient coffee shop / bakery in the lobby.
Reviewed on May 18, 2026
The Talbott, Autograph Collection
Downtown Chicago
Price was CA $1,574, price is now CA $1,063 per person
CA $1,063
per person
Jun 27 - Jul 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (116 reviews)
We thoroughly enjoyed our stay. The location was excellent, conveniently close to everything we needed. The room was spacious and spotless. The breakfast was fantastic, offering a wide variety of options to choose from.
Reviewed on May 17, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,603, price is now CA $1,099 per person
CA $1,099
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,507 reviews)
I’m not sure if the hotel had a lack of staff but I called for towels and never received any, the next day they brought towels shortly after I called again.
Reviewed on May 21, 2026
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Price was CA $1,330, price is now CA $941 per person
CA $941
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.2/10 Very Good! (2,711 reviews)
A decent buisness class hotel. No frills. Rooms are smaller, the queen beds are not true queens, and much smaller.
Reviewed on May 22, 2026
Midlothian Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $185 per night from May 25 to May 26
CA $185
CA $219 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (10,132 reviews)
"Did not have hot water when we returned to room after concert. Next morning called and maintenance came to fix. Good location to walk to South Shore train station and Grant Park"
Reviewed on May 23, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $220 per night from May 27 to May 28
CA $220
CA $301 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,214 reviews)
"One of the best hotels I’ve stayed in!"
Reviewed on May 23, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $168 per night from May 25 to May 26
CA $168
CA $199 total
May 25 - May 26
includes taxes & fees
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.
Discover the most popular places to visit in Midlothian
Wrigley Field
4.5/5(159 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(3 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4.5/5(460 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Midlothian
Skydeck - Willis Tower Admission
CA $60
per adult
96% of travellers recommend
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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.
