
Frankfort Vacation Packages
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Your Frankfort Vacation
Organizing your next big escape is a breeze with a Frankfort vacation package. The neighborhood of Flossmoor, which is great for golfing, makes a superb base to discover the wonders of this vibrant city. Make your trip to Frankfort even more fun and exciting by going sightseeing. Hollywood Casino Amphitheatre, Odyssey Fun World and Green Garden Country Club are some of the leading attractions you'll want to explore. That dream Frankfort vacation is a few clicks away. Explore accommodations, flights and more on Expedia for a getaway that's tailored to suit your style.
Top Frankfort Vacation Deals
Price found within the past 48 hours. Click for updated prices.

Le Méridien Essex Chicago
Downtown Chicago
Price was CA $1,442, price is now CA $1,030 per person
CA $1,030
per person
Aug 5 - Aug 9
found 14 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.8/10 Excellent! (1,004 reviews)
Staff was attentive and friendly. Atmosphere was welcoming. Restaurant had a great selection food was good and prices reasonable. Rooms were comfy.
Reviewed on Apr 23, 2026

ENVITAE Hotel 4 Bedroom Luxury Apartments
Near North Side
Price was CA $4,301, price is now CA $2,954 per person
CA $2,954
per person
Jul 21 - Jul 27
found 2 hours ago
Roundtrip flight included
Toronto (YYZ) to Chicago (ORD)
9.6/10 Exceptional! (16 reviews)
⭐⭐⭐⭐⭐
We had a fantastic stay in this 4-bedroom apartment hotel. Looks exactly like the pictures. The unit was spotlessly clean and perfectly appointed — it truly felt like a home away from home. The kitchen had every amenity you could possibly need, which made cooking and relaxing with family incredibly easy.
The bedding was beautiful and very comfortable, and having a washer and dryer in the unit was a huge bonus, especially for a longer stay.
The building itself felt very secure, including the parking area, which gave us great peace of mind. We also loved the amenities — the gym and lounge area were excellent and well maintained.
Overall, this was one of the best apartment-style stays we’ve had. Comfortable, convenient, and thoughtfully set up. We would absolutely stay here again.
Reviewed on Mar 5, 2026


Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was CA $1,502, price is now CA $1,039 per person
CA $1,039
per person
Jul 1 - Jul 4
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on May 8, 2026

Kimpton Gray Hotel by IHG
Downtown Chicago
Price was CA $2,244, price is now CA $1,564 per person
CA $1,564
per person
Jul 31 - Aug 3
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
The morning coffee was excellent. We asked about tea in the evening and akettle and wonderful teas were brought to our room. We went to the bar for happy hour and the appetizers were great as were the prices. Nice location. Friendly staff.
Reviewed on May 12, 2026
Frankfort Hotel Deals

Sleep Inn Midway Airport Bedford Park
6650 S Cicero Ave Chicago IL
Fully refundable
The price is CA $141 per night from May 25 to May 26
CA $141
CA $165 total
May 25 - May 26
includes taxes & fees
8/10 Very Good! (1,866 reviews)
Breakfast was good.
Reviewed on May 11, 2026

Holiday Inn Chicago – Midway Airport S by IHG
7353 S Cicero Avenue Chicago IL
Fully refundable
The price is CA $185 per night from May 24 to May 25
CA $185
CA $231 total
May 24 - May 25
includes taxes & fees
8.2/10 Very Good! (1,000 reviews)
It was in a good location right next to a bus stop but it looked like they were fixing the place up and I’m sure it will be great when it’s done but it’s not there yet
Reviewed on May 9, 2026

DoubleTree by Hilton Chicago - Alsip
5000 W 127th St Alsip IL
Fully refundableReserve now, pay when you stay
The price is CA $166 per night from May 25 to May 26
CA $166
CA $187 total
May 25 - May 26
includes taxes & fees
8.4/10 Very Good! (1,045 reviews)
Clean room with comfortable bed. No complimentary breakfast. No microwave in room. Pool closed. Parking was good. If there was a fitness room I couldn’t find it. Outside visiting area very convenient.
Reviewed on May 11, 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.
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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.







