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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
per person
Jul 5 - Jul 11
Roundtrip non-stop flight included
Tokyo (TYO) to Chicago (ORD)
8.8/10 Excellent! (205 reviews)
Thoroughly enjoyed my stay and my room. Will definitely book here again. Basic view of the courtyard but that was not important to me.
Reviewed on Mar 16, 2024
Trump International Hotel & Tower Chicago
Downtown Chicago
per person
Jul 30 - Aug 3
Roundtrip non-stop flight included
Tokyo (NRT) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
Just comparing it to always staying at the Peninsula. The 5 star service wasn’t near as good and it was just stuffy. The workers weren’t near as nice and welcoming.
Reviewed on May 13, 2024
Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Downtown Chicago
4 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.
Chicago Hotel Deals
Warwick Allerton - Chicago
701 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥17,915 per night from May 27 to May 28
¥17,915
per night
May 27 - May 28
7.6/10 Good! (2,578 reviews)
"Nice view. Great location. I just bounced in and out for a concert but I would totally stay here again."
Reviewed on May 12, 2024
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥24,260 per night from May 14 to May 15
¥24,260
per night
May 14 - May 15
7.6/10 Good! (6,713 reviews)
"The Congress is a short wall to the Symphony, and the art museum. It's an old hotel but clean and everything worked. Mattresses were a little too firm for me."
Reviewed on May 11, 2024
The Westin Michigan Avenue Chicago
909 North Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is ¥32,558 per night from May 27 to May 28
¥32,558
per night
May 27 - May 28
8.6/10 Excellent! (1,007 reviews)
"We had a wonderful time in Chicago! This property was located in such a great area and easy walking to all the things we wanted to do...and eat. :)"
Reviewed on May 10, 2024
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
Discover the most popular places to visit in Chicago
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
McCormick Place
4.5/5(1,805 reviews)
Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.
Six Flags Great America
4.5/5(347 reviews)
Spend a day at this sprawling theme park to enjoy an array of thrilling roller coaster rides, a water park and entertainment for kids of all ages.
What to do in Chicago
Odyssey Lake Michigan Premier Dinner Cruise
¥27,764
Per adult
76% of travellers recommend
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Hotels
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Flights
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.