Jefferson Park Holidays

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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.

Price found within the past 48 hours. Click for updated prices.
  • Breakfast and dinner served
    Aug 14 - Aug 16

    Omni Chicago Hotel + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.2/10 - Wonderful (1,789 reviews)
    "Booked a room - got a suite! Enjoyed the extra space. A separate living room for watching TV or working at a desk. Staff at the hotel was very helpful. Enjoyed the breakfast too."
    Reviewed June 3, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$991
    AU$739
    per traveller
    found 1 day ago
    Omni Chicago Hotel
  • Serves breakfast, lunch and dinner
    Aug 14 - Aug 16

    JW Marriott Chicago + Flight

    Downtown Chicago
    2 nights
    4.5 star property
    9.2/10 - Wonderful (1,001 reviews)
    "Good customer service and the food in the lobby restaurants was so good! Also the service at that restaurant is amazing I believe her name was Stephanie, she went out of her way to find me caffeine free Diet Coke. Also, we forgot to tell them that we don’t eat bacon after the hamburger came. They happily to get back and started another hamburger to make sure there’s no bacon residue in it."
    Reviewed May 31, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$1,110
    AU$806
    per traveller
    found 1 day ago
    JW Marriott Chicago
  • Premium bedding, pillow-top beds, in-room safe, individually furnished
    Aug 14 - Aug 16

    Level Chicago - River North + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    9.2/10 - Wonderful (1,011 reviews)
    "I recommend 1000/10, this hotel has everything you need and the location is everything. LOVE LOVE LOVE."
    Reviewed June 3, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$1,094
    AU$825
    per traveller
    found 1 day ago
    Level Chicago - River North
  • Terrace/patio
    Aug 14 - Aug 16

    Trump International Hotel & Tower Chicago + Flight

    Downtown Chicago
    2 nights
    5.0 star property
    9.6/10 - Exceptional (1,878 reviews)
    "Great room, professional staff, no complaints."
    Reviewed May 31, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    Save 100% on your flight
    AU$1,591
    AU$1,200
    per traveller
    found 1 day ago
    Trump International Hotel & Tower Chicago
  • Lobby
    Aug 14 - Aug 16

    Hotel Felix River North/Magnificent Mile + Flight

    Downtown Chicago
    2 nights
    4.0 star property
    8.2/10 - Very good (2,750 reviews)
    "Hotel staff was super nice. Great location to be in walking distance of a lot of places."
    Reviewed June 3, 2026
    Return • New York (LGA) - Chicago (ORD)
    LGA - ORD • Direct ORD - JFK • Direct
    AU$1,034
    AU$781
    per traveller
    found 1 day ago
    Hotel Felix River North/Magnificent Mile

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

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 29 June to 30 June
AU$231
29 June - 30 June
includes taxes & fees
8/10 Very Good! (10,164 reviews)
"The location was excellent. Close to all the museums, shopping district and river walk."

Reviewed on 3 June 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 refundableReserve now, pay when you stay
The price is AU$252 per night from 28 June to 29 June
AU$252
28 June - 29 June
includes taxes & fees
7.8/10 Good! (1,509 reviews)
"Clean room"

Reviewed on 3 June 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 AU$355 per night from 30 June to 1 July
AU$355
30 June - 1 July
includes taxes & fees
9.4/10 Exceptional! (4,329 reviews)
"Great rooftop bar and breakfast."

Reviewed on 3 June 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

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

Activities

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

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

Art Institute of Chicago

AU$55
per adult
92% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

AU$56
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.