Jefferson Park Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • 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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    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Jefferson Park

Price found within the past 48 hours. Click for updated prices.
Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
Downtown Chicago
Price was CA $913, price is now CA $671 per person
CA $671
per person
Jan 21 - Jan 24
just found
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
I really loved this hotel. The rooms were clean and spacious. The staff was nice and helpful James was especially great. The restaurant staff was very helpful. When I visit again I'll stay here. And it was close to everything.

Reviewed on Nov 3, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was CA $1,898, price is now CA $1,336 per person
CA $1,336
per person
Jan 21 - Jan 24
just found
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,394, price is now CA $992 per person
CA $992
per person
Dec 19 - Dec 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $1,801, price is now CA $1,315 per person
CA $1,315
per person
Jan 21 - Jan 24
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was CA $1,344, price is now CA $983 per person
CA $983
per person
Jan 21 - Jan 24
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,161 reviews)
The building and hotel are gorgeous, the staff were so kind and friendly, the carbon suite was clean and had an exceptional view, and the in room dining was delicious. Amazing experience, def will be back.

Reviewed on Nov 8, 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
A busy city street with tall buildings, a bus, and cars.

Downtown Chicago

4 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 $164 per night from Nov 23 to Nov 24
CA $164
CA $195 total
Nov 23 - Nov 24
includes taxes & fees
8/10 Very good! (10,151 reviews)
"The room was clean but tiny. Checkin was quick and they let us check in early. One thing I didn’t like is that we couldn’t control the thermostat. The location is awesome- close to everything!"

Reviewed on Nov 10, 2026

Congress Plaza Hotel
The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

4 out of 5
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $164 per night from Nov 23 to Nov 24
CA $164
CA $195 total
Nov 23 - Nov 24
includes taxes & fees
8/10 Very good! (2,695 reviews)
"Love this hotel! It was really nice, staff were very friendly and helpful! Restaurant and bar were perfect and open late. Paid breakfast buffet was nice as well!"

Reviewed on Nov 10, 2026

The Chicago Hotel Collection Ambassador Gold Coast
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 $150 per night from Dec 10 to Dec 11
CA $150
CA $178 total
Dec 10 - Dec 11
includes taxes & fees
River Hotel
See all 4,742 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 $671. 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.

Stay near popular Jefferson Park attractions

Copernicus Center

You can make plans for a show at Copernicus Center during your trip to Chicago. Amble around this vibrant area's lakeside or attend a sporting event.
See properties

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $34
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Skydeck Chicago at Willis Tower

Skydeck Chicago at Willis Tower

CA $60
per adult
84% of travellers recommend
Skydeck Chicago at Willis Tower
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

CA $57
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
See all activities in Chicago
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.