Jefferson Park Vacation Packages

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  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Holiday Package Deals in Jefferson Park

Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town

Level Chicago – Old Town

4 out of 5
Downtown Chicago
Price was CA $1,584, price is now CA $1,066 per person
CA $1,066
per person
Jul 3 - Jul 6
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9/10 Wonderful! (472 reviews)
Beautiful clean place. Great safe location within proximity to restaurants and transportation around the city with fantastic views. Would recommend and stay here again.

Reviewed on May 14, 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was CA $2,200, price is now CA $1,425 per person
CA $1,425
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
9.2/10 Wonderful! (471 reviews)
The rooms were very clean!

Reviewed on May 4, 2026

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
Downtown Chicago
Price was CA $2,145, price is now CA $1,440 per person
CA $1,440
per person
Jun 19 - Jun 23
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,489 reviews)
Amazing hotel. I would stay again.

Reviewed on May 15, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was CA $2,205, price is now CA $1,494 per person
CA $1,494
per person
Jun 24 - Jun 29
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Chicago (ORD)
8.4/10 Very Good! (1,825 reviews)
Lovely hotel, very modern and clean. Had fantastic views from the top floor. We were on floor 28 and the skyline was great. Bed very comfortable and it was expected from a 4* hotel. Chicago is a business city, reminded me of a bar man set as its high rised buildings and slightly darker from the shadows of these buildings. Locally there was a few cafes and coffee shops for easy reach for breakfast

Reviewed on May 11, 2026

ENVITAE Hotel 4 Bedroom Luxury Apartments

ENVITAE Hotel 4 Bedroom Luxury Apartments

2 out of 5
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 1 day 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

Where to stay in Jefferson Park

Find the best Jefferson Park areas and neighborhoods for the activities you enjoy most. Learn more about Jefferson Park
Downtown Chicago

Downtown Chicago

5 out of top 10 points of interest in this area

The heart of the Midwest’s glittering metropolis has many offerings, from shopping and dining to parks, museums and exciting contemporary public art.

Find hotels in Downtown Chicago

Jefferson Park 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
The price is CA $183 per night from May 26 to May 27
CA $183
CA $218 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,121 reviews)
Only thing bad about this is they don’t have parking and parking was $65

Reviewed on May 15, 2026

Congress Plaza Hotel
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $197 per night from May 25 to May 26
CA $197
CA $234 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,175 reviews)
Hotel is a beautiful, smaller boutique property.

Reviewed on May 14, 2026

River Hotel
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $204 per night from May 25 to May 26
CA $204
CA $282 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,146 reviews)
Great location. Comfy bed. Rooftop bar really nice! Friendly service.

Reviewed on May 15, 2026

Hotel Riu Plaza Chicago
See all 4,935 properties in Jefferson Park
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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Frequently asked questions

How much does a Jefferson Park vacation package cost?
From as little as CA $1,066. Yes, you read that right. Our Jefferson Park vacation packages are a great way to stretch your budget further. Bundle your hotels, flights and car rentals and get to know this popular destination.
How do I get a cheap travel package to Jefferson Park?
Bundle your hotels and flights with Expedia to save big bucks on your next getaway. With over 550 partner airlines and 1,000,000 hotels across the globe, your Jefferson Park vacation package can be customized exactly to suit your travel style. With all that extra money, why not include one or more fun activities and tours? It's an easy way to unlock even more savings. The vacation you've always dreamed of in Jefferson Park is closer than you thought!
Where should I stay in Jefferson Park?
Cross Lincoln Park off your bucket list and then stay moments from it. Experience the lively atmosphere around this top attraction and check it out whenever you please!
How far in advance should I book my Jefferson Park vacation?
It all depends on the air carrier, but it's usually possible to look up international flights on Expedia up to a year in advance. While it's generally recommended to book ahead of time, lucky travelers will sometimes nab a cheaper ticket only weeks before their intended journey.
What does an Expedia Jefferson Park travel package include?
With Expedia, you can choose any combination of car rentals, hotels and flights to create your ideal Jefferson Park package. Once you've made your booking, you can add on fun stuff like sightseeing tours and activities. Remember — the more you bundle, the more discounts you'll get!
What should I know before booking a Jefferson Park travel package?
Whether it's relaxation or adventure you're seeking, a Jefferson Park vacation package lets you plan your escape your way. Plus, you'll get access to great discounts just for combining your hotel with your rental car and flights. The more you bundle, the bigger the savings!
Can I choose my airline with a Jefferson Park Expedia vacation package?
Yes — that's one of the best things about an Expedia package. You get to choose. We have access to more than 550 airline partners throughout the world, so you have lots of choice when planning your Jefferson Park getaway.
If I'm not able to travel, can I cancel my Jefferson Park vacation package?
Yes, you can cancel your Jefferson Park booking if your travel plans have been upended. Whether you'll incur a penalty or not depends on your airline, hotel or car rental company. You may be able to change or cancel your booking free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.