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.
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $2,594, price is now CA $1,678 per person
CA $1,678
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes.
Reviewed on May 28, 2026
Level Chicago - River North
Downtown Chicago
Price was CA $1,878, price is now CA $1,339 per person
CA $1,339
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,017 reviews)
Everything was amazing! The women at the front desk, specifically Joy and Makaya, absolutely wonderful! Our day was perfect. Everything was considered and I have zero complaints. Absolutely will stay here again.!!
Reviewed on May 29, 2026
Level Chicago – Old Town
Downtown Chicago
Price was CA $1,761, price is now CA $1,258 per person
CA $1,258
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Staff was amazing and the apartment building was phenomenally clean!
Reviewed on May 28, 2026
The Langham, Chicago
Downtown Chicago
Price was CA $2,318, price is now CA $1,683 per person
CA $1,683
per person
Jul 10 - Jul 13
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
10/10 experience! Love this hotel!…the only negative was a less than nice /helpful staff person at the front desk of the spa when I asked about the use of the sauna/steam room and also my neighbors next to my room were quite loud
Reviewed on May 27, 2026
Midlothian Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Jun 29 to Jun 30
CA $179
CA $213 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,124 reviews)
"Great location and clean"
Reviewed on May 29, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $296 per night from Jun 29 to Jun 30
CA $296
CA $392 total
Jun 29 - Jun 30
includes taxes & fees
9.4/10 Exceptional! (4,287 reviews)
"Nice place"
Reviewed on May 29, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
The price is CA $210 per night from Jun 28 to Jun 29
CA $210
CA $249 total
Jun 28 - Jun 29
includes taxes & fees
7.8/10 Good! (1,487 reviews)
"rooftop"
Reviewed on May 29, 2026
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.
Michigan Avenue
4.5/5(20 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.
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.
