Jefferson Park Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

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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.
Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was CA $1,794, price is now CA $1,126 per person
CA $1,126
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
8.6/10 Excellent! (1,873 reviews)

The Emily Hotel

The Emily Hotel

4 out of 5
Downtown Chicago
Price was CA $1,734, price is now CA $1,158 per person
CA $1,158
per person
Dec 19 - Dec 25
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.2/10 Wonderful! (1,358 reviews)
Great location in the West Loop. The rooms are big and the beds are comfy. We’ve stayed there three times. The outdoor theatre shows great films and has an outdoor bar. Coffee shop is in the lobby. There’s not really a fun bar, but lots of places to have cocktails in the neighborhood. A lobby fireplace would be a nice addition in the lobby for cold Chicago nights.

Reviewed on Nov 13, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was CA $4,165, price is now CA $2,806 per person
CA $2,806
per person
Jan 22 - Jan 25
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.8/10 Exceptional! (1,000 reviews)

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Price was CA $3,057, price is now CA $2,112 per person
CA $2,112
per person
Dec 28 - Jan 2
found 23 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
This place was amazing and the hotel staff was extremely helpful

Reviewed on Nov 10, 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 $1,820, price is now CA $1,271 per person
CA $1,271
per person
Jan 22 - Jan 25
found 2 hours ago
Roundtrip flight included
Toronto (YTO) to Chicago (ORD)
9.4/10 Exceptional! (2,739 reviews)

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 cityscape with tall skyscrapers and a historic tower.

Downtown Chicago

4 out of top 10 points of interest in this area

Known for its fascinating museums, stunning river views, and gorgeous architecture, there's plenty to explore in Downtown Chicago. Top attractions like Navy Pier and Michigan Avenue are major draws. Catch the metro at State Station or Clark-Lake Station to see more of the city.

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
The price is CA $166 per night from Nov 22 to Nov 23
CA $166
CA $197 total
Nov 22 - Nov 23
includes taxes & fees
8/10 Very good! (10,081 reviews)
"Room stunk very bad staff refused to upgrade or give another room. Unsatisfied stay, DO NOT RECOMMEND."

Reviewed on Nov 14, 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
The price is CA $165 per night from Dec 6 to Dec 7
CA $165
CA $197 total
Dec 6 - Dec 7
includes taxes & fees
The Chicago Hotel Collection Ambassador Gold Coast
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
The price is CA $144 per night from Nov 24 to Nov 25
CA $144
CA $171 total
Nov 24 - Nov 25
includes taxes & fees
8.8/10 Excellent! (5,617 reviews)
"Amazing spot right in the middle of the action, shopping to the north and attractions to the south. The river right beside the hotel and the lake a short walk away. My room was a little tight but I am not in Chicago to be in my room. Would stay here again in a heartbeat."

Reviewed on Nov 14, 2026

River Hotel
See all 4,750 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 $1,126. 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.