Far North Side Vacations from ￥356,691
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The Latest Far North Side Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
￥456,116
per person
Nov 14 - Nov 20
found 20 hours ago
Roundtrip non-stop flight included
Osaka (OSA) to Chicago (ORD)
9.6/10 Exceptional! (2,003 reviews)
The Trump Hotel In Chicago is one of my family's FAVORITE hotels in the world. We stay at The Trump every single time we're in Chicago. It's the BEST.😀👍
Reviewed on Sep 2, 2026
Where to stay in Far North Side
Find the best Far North Side areas and neighborhoods for the activities you enjoy most. Learn more about Far North Side
Lincoln Square
1 out of top 10 points of interest in this area
When in Lincoln Square and the surrounding area, you'll want to check out sights like Swedish American Museum Center or Riviera Theatre and hop on the metro to see more the city at Western Station (Brown Line) or Rockwell Station.
West Ridge
The restaurants and shopping are just a few features travelers like about West Ridge. If you want to do some sightseeing nearby, Emil Bach House and North Shore Beach Park are a few top places to visit.
Ravenswood
Get to know Ravenswood and its many features like its restaurants and art galleries. You might want to explore sights like Neo-Futurists and Black Ensemble Theater, and you can jump on the metro at Damen Station (Brown Line) or Western Station (Brown Line) to get around the city.
Andersonville
If you're spending some time in Andersonville, Swedish American Museum Center and Andersonville Galleria are top sights worth seeing.
Norwood Park
Even though there aren't top sights in Norwood Park, you can explore the larger area and take in top sights like Milwaukee Avenue. Jump on the metro at Harlem-O'Hare Station to see more of the city.
Find the Best Far North Side Vacation Packages
Far North Side Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
￥16,398
￥19,495 total
Sep 7 - Sep 8
includes taxes & fees
8/10 Very Good! (10,259 reviews)
"It’s a classic Chicago hotel. It’s was clean and comfortable. Also a great location for walking to downtown parks and food!"
Reviewed on Sep 3, 2026
The Chicago Hotel Collection Ambassador Gold Coast
1301 N State Pkwy Chicago IL
Fully refundableReserve now, pay when you stay
￥19,296
￥22,941 total
Sep 8 - Sep 9
includes taxes & fees
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.
Stay near popular Far North Side attractions
Aragon Ballroom
9.2/10 (10 reviews)
Catch an event at Aragon Ballroom during your trip to Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
Montrose Harbor
With trails, a beach and a bird sanctuary, this spacious city harbor is a good place to sail from and a great place to hang out.
Hutchinson Street Historic District
You can learn about the history of Chicago when you stop by Hutchinson Street Historic District. Experience the acclaimed art scene and entertainment choices in this vibrant area.
Riviera Theatre
8.0/10 (1 review)
You can enjoy a show at Riviera Theatre during your stay in Chicago. Amble around this vibrant area's lakeside or experience its acclaimed art scene.
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.
Pegasus Players
You can get tickets for a performance at Pegasus Players during your trip to Chicago. Experience the acclaimed art scene and entertainment choices in this vibrant area.
Leather Archives & Museum
You can spend an afternoon exploring the galleries in Leather Archives & Museum in Chicago. Stroll along the beautiful beaches or experience the acclaimed theater scene in this vibrant area.
Grandparents Park
Grandparents Park is just one of the places to see in Chicago, so why not enjoy the other things to explore during your travels? Stroll along the lakeside or attend a sporting event in this vibrant area.
What to do in Far North Side
Chicago: Willis Tower Skydeck and The Ledge Ticket
￥7,453
per adult
88% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
￥6,484
per adult
94% of travellers recommend
Frequently asked questions
How much does a Far North Side vacation package cost?
Tailor make your Far North Side vacation package from only ￥356,691. Pick from any combination of rental cars, flights and hotels to build the getaway you've been dreaming about. Don't forget to add on a few experiences or tours!
How do I get a cheap travel package to Far North Side?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, rental cars, flights and activities — we've got them all. Pick a combination that suits you and see your savings stack up. Of course, a travel package is never a one-size-fits-all. That's why we offer more than 550 air carriers and 1,000,000 properties throughout the world, which lets you customize your Far North Side getaway.
How far in advance should I book my Far North Side vacation?
It can be tricky to know when the best time is to book your Far North Side vacation. But usually the earlier you book, the cheaper the prices. In some cases, you can reserve your flights and hotels up to a year prior to departure. If you're thinking of a last-minute getaway, no need to stress! There are fantastic bargains announced on Expedia every day.
What does an Expedia Far North Side travel package include?
From flights and hotels to car rentals, Expedia can help you put together a Far North Side package that's perfect for you. Vacationing for a few weeks? Check out a rental car, hotel and flight bundle. If your break is short, a hotel and airfare deal could be more your style. Experiences can also be added after you've booked. Our travel packages make it simple to plan and save.
What should I know before booking a Far North Side travel package?
Our prices are always low. However, you'll enjoy even more bargains if you book your hotels, flights and car rentals together. With an Expedia travel package, you'll get transparent pricing and lots of choice.
Can I choose my airline with a Far North Side Expedia vacation package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines throughout the world. Our vacation packages give you the freedom to take your pick of available flight, hotel or activity options that suit you.
If I'm not able to travel, can I cancel my Far North Side vacation package?
Your situation can change unexpectedly, so yes. You may be able to change or cancel your Far North Side vacation package for free within 24 hours of booking. For bookings made more than 24 hours ago, you can still cancel or make changes, but your car rental company, hotel or airline may charge a fee. Want more information? Take a look at our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
