Jefferson Park Vacations from ￥387,046

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    Save up to ￥109,000 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.
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was ￥462,078, price is now ￥387,046 per person
￥387,046
per person
Jun 16 - Jun 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,692 reviews)
Great property and location!

Reviewed on May 8, 2026

The Peninsula Chicago

The Peninsula Chicago

5 out of 5
Downtown Chicago
Price was ￥803,525, price is now ￥639,790 per person
￥639,790
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.8/10 Exceptional! (1,006 reviews)
Loved the location. Loved the property , staff, amenities, and service. I did not live the brutal Chicago cold. Four below is just hateful cold weather. Want to return this summer or fall to enjoy the area. Excellent property. Definitely recommend you stay if in Chicago.

Reviewed on May 10, 2026

Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was ￥513,296, price is now ￥410,293 per person
￥410,293
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (3,991 reviews)
Was a really nice hotel. My only concerns was the phones in the room didn’t work. No way to call front desk, front people weren’t super helpful and there was no microwave. Rooftop bar and room were excellent

Reviewed on May 10, 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was ￥632,616, price is now ￥511,244 per person
￥511,244
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Horrible, horrible housekeeping staff many times I had to have head of housekeeping come and monitor Very disappointing

Reviewed on May 10, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was ￥499,432, price is now ￥403,632 per person
￥403,632
per person
Aug 4 - Aug 9
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
9/10 Wonderful! (3,303 reviews)
The view is fantastic. You can see the Chicago river on one side, abd skyscraper on tge other side. The small items that the hotel provides, makes the stay, pleasant and homely.

Reviewed on May 10, 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

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 ￥20,926 per night from May 12 to May 13
￥20,926
￥24,880 total
May 12 - May 13
includes taxes & fees
8/10 Very Good! (10,207 reviews)
Clean room, good staff

Reviewed on May 11, 2026

Congress Plaza Hotel
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 ￥23,344 per night from May 25 to May 26
￥23,344
￥32,216 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,106 reviews)
Was a really nice hotel. My only concerns was the phones in the room didn’t work. No way to call front desk, front people weren’t super helpful and there was no microwave. Rooftop bar and room were excellent

Reviewed on May 10, 2026

Hotel Riu Plaza 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 ￥23,417 per night from May 25 to May 26
￥23,417
￥27,841 total
May 25 - May 26
includes taxes & fees
9/10 Wonderful! (4,293 reviews)
The hotel staff is excellent! Very friendly and very helpful. The hotel is very clean and well maintained. The only issue I had was the charging ports and electrical sockets next to our bed did not work which made overnight charging of our phones and watches difficult.

Reviewed on May 10, 2026

Hilton Chicago/Magnificent Mile Suites
See all 4,928 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 ￥387,046. 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

￥4,289
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

￥7,012
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
Art Institute of Chicago

Art Institute of Chicago

￥6,375
per adult
92% of travellers recommend
Art Institute of Chicago
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.