Chicago Vacations from NT$30,325
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Staypineapple, An Iconic Hotel, The Loop
Downtown Chicago
Price was NT$38,664, price is now NT$30,325 per person
NT$30,325
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (1,054 reviews)
The staff were fantastic, and the beds were insanely comfortable/blankets were soft and plush. The location is advantageous- lots of shopping, food, and things to do nearby. Getting an Uber from this location was a breeze and took less than five minutes. The Valet service for Staypineapple was also good. Would definitely recommend!
Reviewed on 2026/5/1
Hotel Riu Plaza Chicago
Downtown Chicago
Price was NT$52,839, price is now NT$37,068 per person
NT$37,068
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Beautiful hotel, very impressed with the cleanliness, space in the room and the breakfast. So pleased we chose this hotel as the location was excellent 👌
Reviewed on 2026/5/7
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Price was NT$58,124, price is now NT$43,004 per person
NT$43,004
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
If you plan on staying in this hotel by all means the view is great, but if you plan on moving your vehicle at all the hotel does not validate In-N-Out parking. You have to pay every time you want to leave and come back. Unlike the normal hotel, La Quinta downtown Chicago validate parking yes it’s $70 but you can drive in and out as many times as you want during your stay. Unlike this hotel.
Reviewed on 2026/5/8
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was NT$69,088, price is now NT$52,176 per person
NT$52,176
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (1,863 reviews)
Incredible everything
Reviewed on 2026/5/8
Le Méridien Essex Chicago
Downtown Chicago
Price was NT$47,870, price is now NT$37,258 per person
NT$37,258
per person
Jul 12 - Jul 16
found 1 day ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
8.8/10 Excellent! (1,003 reviews)
Staff was attentive and friendly. Atmosphere was welcoming. Restaurant had a great selection food was good and prices reasonable. Rooms were comfy.
Reviewed on 2026/4/23
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.
Find the Best Chicago Vacation Packages
Chicago Hotel Deals
Hotel Felix River North/Magnificent Mile
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$2,712 per night from May 20 to May 21
NT$2,712
NT$4,183 total
May 20 - May 21
includes taxes & fees
8.2/10 Very Good! (2,696 reviews)
great location
Reviewed on 2026/5/9
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,194 per night from May 10 to May 11
NT$4,194
NT$4,986 total
May 10 - May 11
includes taxes & fees
8/10 Very Good! (10,189 reviews)
Room was clean, coffee maker didn’t work but was replaced quickly. Staff all very helpful, especially Steve the doorman/security. Very helpful getting us a cab!
Reviewed on 2026/5/8
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,681 per night from May 25 to May 26
NT$4,681
NT$6,460 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (4,091 reviews)
Everyone at this hotel was in extremely helpful. It was definitely worth the price. One of the biggest breakfast buffets I have ever seen at a hotel. The hotel was very clean and quiet for the most part. The only downfall was there was no parking but we just used public transportation. Would highly ...
Reviewed on 2026/5/8
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.
Discover the most popular places to visit in Chicago
Wrigley Field
4.5/5(2,149 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
Naval Base Great Lakes
4.5/5(461 reviews)
After visiting Naval Base Great Lakes, make a plan to see the other sights and activities in North Chicago. Wander the lakeside in this family-friendly area.
Navy Pier
4.5/5(4,925 reviews)
A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Explore a world of travel with Expedia
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- Merchandise Mart
- Chicago Theatre
- Prentice Women's Hospital
- Willis Tower
- Art Institute of Chicago
- Chicago Children's Museum
- Water Tower Place
- Cooking & Hospitality Institute of Chicago
- Oak Street Beach
- Shops at North Bridge
- Crown Fountain
- Visit Greektown
- Northwestern Memorial Hospital
- Visit Chicago
- Buckingham Fountain
- Gold Coast Vacations
- Afrocentric Bookstore
- Navy Pier
- Chicago Riverwalk
- Museum of Contemporary Art Chicago
- 333 West Wacker Drive
- State Street
- Harold Washington Library Center
- Millennium Park
- Bridgehouse and Chicago River Museum
- Newberry Library
- The East Bank Club
- 311 S Wacker Dr
- Visit Downtown Chicago
- Grant Park
- Chicago City Hall
- Vietnam Veterans Memorial
- Film Row Cinema
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- Car rentals near Chicago
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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.
