Jefferson Park Holidays from AU$808

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Your Jefferson Park Holiday

From its festivals to its culture, there are so many things to like about Jefferson Park. Book a customised Jefferson Park holiday package and prepare to fall for the delights of this neighbourhood. Some popular nearby attractions to check out during your trip to Jefferson Park include Milwaukee Avenue, Northwestern College Chicago Campus and Monument Park. Whatever your ideal Jefferson Park holiday looks like, you can make it a reality with Expedia.

Top Holiday Package Deals in Jefferson Park

Price found within the past 48 hours. Click for updated prices.
The Drake

The Drake

4 out of 5
Downtown Chicago
Price was AU$1,183, price is now AU$808 per person
AU$808
per person
16 Nov - 19 Nov
found 19 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
8.8/10 Excellent! (1,291 reviews)
Great location and wonderful staff. Stayed with my family of four and we were able to easily get to all the wonderful sites we wanted to visit. The historic charm and lastige spaces enhanced our stay and our breakfast was superb.

Reviewed on 14 Oct 2025

Park Hyatt Chicago

Park Hyatt Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$1,974, price is now AU$1,358 per person
AU$1,358
per person
16 Nov - 19 Nov
found 19 hours ago
Return flight included
Raleigh (RDU) to Chicago (ORD)
9.6/10 Exceptional! (1,002 reviews)
The front desk staff was super friendly and helpful. After waking up at 4am to catch an early flight, we were thrilled when they had a room ready for us for early check-in. Hyatt does a great job with room lay-outs. It was obvious that our room was recently renovated with a modern conveniences like motorized shades, a comfy window seat, hidden bar and Nespresso maker, and clean decor. Our friends were staying around the corner at the Ritz and liked our room better.

Reviewed on 14 Oct 2025

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was AU$2,045, price is now AU$1,417 per person
AU$1,417
per person
16 Nov - 19 Nov
found 19 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9.4/10 Exceptional! (1,716 reviews)
Excellent luxury atmosphere with second to none customer service. The bathroom was very nice. Although the toilet has a slight odor that was unexpected for the high quality room and hotel.

Reviewed on 15 Oct 2025

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,193, price is now AU$850 per person
AU$850
per person
16 Nov - 19 Nov
found 19 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9/10 Wonderful! (2,765 reviews)
Hotel was clean and staff was friendly.

Reviewed on 15 Oct 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was AU$1,417, price is now AU$1,025 per person
AU$1,025
per person
16 Nov - 19 Nov
found 19 hours ago
Return flight included
Greensboro (GSO) to Chicago (ORD)
9.4/10 Exceptional! (1,085 reviews)
I loved the hotel, however I would request an inside room next time. It was extremely noisy outside.

Reviewed on 11 Oct 2025

Our guide on 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 featuring a city

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

Our pick of the best 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 AU$231 per night from 2 Nov to 3 Nov
AU$231
2 Nov - 3 Nov
includes taxes & fees
8/10 Very Good! (9,398 reviews)
"Was conveniently located"

Reviewed on 13 Oct 2025

Congress Plaza Hotel
Freehand Chicago

Freehand Chicago

4 out of 5
19 East Ohio Street, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$147 per night from 10 Nov to 11 Nov
AU$147
10 Nov - 11 Nov
includes taxes & fees
7.8/10 Good! (2,475 reviews)
"Room needs to be cleaned a little thoroughly and then repainted but generally, I like the place"

Reviewed on 15 Oct 2025

Freehand Chicago
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 16 Nov to 17 Nov
AU$203
16 Nov - 17 Nov
includes taxes & fees
8.8/10 Excellent! (3,088 reviews)
"Clean rooms, great service."

Reviewed on 13 Oct 2025

Hilton Chicago/Magnificent Mile Suites
See all 4,789 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 Holidays
All Inclusive Holidays
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Frequently asked questions

How much does a Jefferson Park holiday package cost?
From as little as AU$808. Yes, you read that right. Our Jefferson Park holiday 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 holiday 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 holiday 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 holiday?
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 travellers 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 holiday 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 holiday 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 holiday 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

Navy Pier

Navy Pier

4.5/5(64 reviews)

A waterfront entertainment strip with fun diversions for both young and old, with shops, restaurants and even a Ferris wheel.

Navy Pier
Millennium Park showing modern architecture, a city and street scenes

Millennium Park

4.5/5(73 reviews)

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Grant Park

Grant Park

4.5/5(47 reviews)

Chicago’s front yard is a pretty landscaped park, which is home to public art displays, museums, themed gardens and international music festivals.

Grant Park

Activities

River tour boat in Chicago

Architecture River Tour

AU$74
per adult
96% of travellers recommend
Architecture River Tour
Skydeck Chicago Admission Ticket

Skydeck - Willis Tower Admission

AU$67
per adult
100% of travellers recommend
Skydeck - Willis Tower Admission
Chicago: Navy Pier Centennial Wheel Regular & Express Ticket

Chicago: Navy Pier Centennial Wheel Ticket

AU$37
per adult
84% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
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.