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*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
  • Indoor wedding
    Aug 21 - Aug 24

    Swissotel - Chicago + Flight

    Downtown Chicago
    3 nights
    4.5 star property
    9.0/10 - Wonderful (3,365 reviews)
    "The gym is on 43 floor.. amazing"
    Reviewed May 31, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,277
    CA $895
    per traveller
    found 1 day ago
    Swissotel - Chicago
  • Front of property
    Aug 12 - Aug 16

    Urban Chicago Oasis + Flight

    Lakeview
    4 nights
    2.0 star property
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $2,463
    CA $1,671
    per traveller
    found 1 hour ago
    Urban Chicago Oasis
  • Seasonal outdoor pool, sun loungers
    Jul 6 - Jul 10

    Hilton Grand Vacations Club Chicago Magnificent Mile + Flight

    Downtown Chicago
    4 nights
    3.5 star property
    9.2/10 - Wonderful (396 reviews)
    "Great location and well maintained property!"
    Reviewed May 29, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,768
    CA $1,239
    per traveller
    found 1 day ago
    Hilton Grand Vacations Club Chicago Magnificent Mile
  • Terrace/patio
    Aug 21 - Aug 24

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    3 nights
    5.0 star property
    9.6/10 - Exceptional (1,892 reviews)
    "Great room, professional staff, no complaints."
    Reviewed May 31, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $2,060
    CA $1,471
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Lobby lounge
    Aug 21 - Aug 24

    Le Méridien Essex Chicago + Flight

    Downtown Chicago
    3 nights
    4.0 star property
    8.8/10 - Excellent (1,002 reviews)
    "Staff was amazing and very helpful, gave us a lot of great recommendations for places to check out and also upgraded our room for free. The room was very nice, a little tight but that is expected in Chicago. Bathroom was perfect great shower, amazing view from room and bathroom window. Very conveniently located, quick walk from the train. Highly recommend and would stay again"
    Reviewed June 1, 2026
    Roundtrip • Montreal (YUL) - Chicago (ORD)
    YUL - ORD • 1 stop ORD - YUL • 1 stop
    CA $1,795
    CA $1,285
    per traveller
    found 1 day ago
    Le Méridien Essex Chicago

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 $192 per night from Jun 29 to Jun 30
CA $192
CA $229 total
Jun 29 - Jun 30
includes taxes & fees
8/10 Very Good! (10,150 reviews)
"Wouldn't stay again unless it's free"

Reviewed on Jun 1, 2026

Congress Plaza Hotel
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is CA $200 per night from Jun 3 to Jun 4
CA $200
CA $238 total
Jun 3 - Jun 4
includes taxes & fees
7.8/10 Good! (1,503 reviews)
"Everything was fine."

Reviewed on Jun 1, 2026

The Chicago Hotel Collection - Magnificent Mile
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 $262 per night from Jun 30 to Jul 1
CA $262
CA $350 total
Jun 30 - Jul 1
includes taxes & fees
9.4/10 Exceptional! (4,315 reviews)
"Everything was great for my stay. Only flaws was that the shower pressures were a bit low and water temperatures were not warm enough to my liking. And maybe fresh squeezed juices instead of the machine ones. Other wise it was good breakfast selection."

Reviewed on Jun 1, 2026

Hotel Riu Plaza Chicago
See all 4,930 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.
All Inclusive Vacations
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Frequently asked questions

How much does a Jefferson Park vacation package cost?
From as little as . 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.

Discover the most popular places to visit in Jefferson Park

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.

Copernicus Center

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

CA $55
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

CA $60
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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.