Jefferson Park Vacations from ￥287,888

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    Save up to ￥45,448 when you book a flight and hotel together*

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The Latest Jefferson Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥340,733, price is now ￥287,888 per person
￥287,888
per person
Jun 12 - Jun 14
found 9 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.4/10 Exceptional! (3,495 reviews)
Great location! Excellent customer service! My only one complaint is that there are no microwaves at this property.

Reviewed on Mar 26, 2026

The Wade

The Wade

4.5 out of 5
Downtown Chicago
Price was ￥442,434, price is now ￥337,288 per person
￥337,288
per person
May 13 - May 18
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.4/10 Very Good! (1,719 reviews)
Enjoyed our stay. Views were amazing and location convenient.

Reviewed on Mar 26, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥568,890, price is now ￥460,718 per person
￥460,718
per person
May 14 - May 18
found 11 hours ago
Roundtrip flight included
Osaka (KIX) to Chicago (ORD)
9.4/10 Exceptional! (1,852 reviews)
Perfect room size for 2+1. The river view was breathtaking especially in the late evening while serenade of colors highlighted other buildings surrounding the Trump Tower hotel. Good food at the restaurant and nice staff helping you to enjoy the memorable time during the visit. We will be back in near future for surr!

Reviewed on Mar 24, 2026

The Neighborhood Hotel-Little Italy

The Neighborhood Hotel-Little Italy

4 out of 5
Near West Side
Price was ￥454,976, price is now ￥387,825 per person
￥387,825
per person
May 28 - Jun 2
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Chicago (ORD)
9.6/10 Exceptional! (238 reviews)
Nice rooms but bedding and pillows were

Reviewed on Mar 24, 2026

DoubleTree by Hilton Chicago - Magnificent Mile

DoubleTree by Hilton Chicago - Magnificent Mile

4 out of 5
Downtown Chicago
Price was ￥354,222, price is now ￥318,869 per person
￥318,869
per person
Jun 8 - Jun 12
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (2,357 reviews)
Everything was good except for not having access to the outdoor space. When we were booking the hotel the outdoor area was one of the reasons the pulled us to stay there. It was not stated that it was unavailable for the season. The pool being closed i get it, but the rest that was featured in the photos was also off limits, the outdoor tents and the grass area.

Reviewed on Mar 26, 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
Downtown Chicago showing 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

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 ￥18,505 per night from Apr 1 to Apr 2
￥18,505
￥21,724 total
Apr 1 - Apr 2
includes taxes & fees
8/10 Very Good! (9,990 reviews)
The room is fine, but I can’t control my AC or heat.

Reviewed on Mar 26, 2026

Congress Plaza Hotel
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 ￥19,474 per night from Apr 9 to Apr 10
￥19,474
￥22,860 total
Apr 9 - Apr 10
includes taxes & fees
9/10 Wonderful! (3,987 reviews)
I would def say please please clean around the pool where the water runs through on the side the stainless steel could use a nice scrub, doesn't look clean at all.

Reviewed on Mar 26, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
Fully refundableReserve now, pay when you stay
The price is ￥23,316 per night from Apr 5 to Apr 6
￥23,316
￥27,371 total
Apr 5 - Apr 6
includes taxes & fees
8.6/10 Excellent! (5,777 reviews)
We ended up with the stomach bug while we were on vacation, but the staff was all so responsive and helpful to us - allowing a later check-out time and bringing us bleach wipes. The texting feature was very helpful!

Reviewed on Mar 26, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 4,862 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.

Frequently asked questions

How much does a Jefferson Park vacation package cost?
From as little as ￥287,888. 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.

Things to do

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

￥3,985
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

￥6,236
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥6,860
per adult
98% 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.