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

Staypineapple, An Iconic Hotel, The Loop

4 out of 5
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 9 hours 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

Hotel Riu Plaza Chicago

4 out of 5
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 9 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (4,070 reviews)
Very centric hotel, would definitely stay here again.

Reviewed on 2026/5/6

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

4 out of 5
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 9 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (2,478 reviews)
My stay was exceptional the staff were very polite and patient, they answered all my questions. I had a very nice view will definitely book again

Reviewed on 2026/5/6

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
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 9 hours ago
Roundtrip flight included
Ontario Intl. Airport (ONT) to Chicago (ORD)
9.4/10 Exceptional! (1,851 reviews)
I love everything in the hotel everything

Reviewed on 2026/5/4

Le Méridien Essex Chicago

Le Méridien Essex Chicago

4 out of 5
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 9 hours 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

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 hotels in Downtown Chicago

Find the Best Chicago Vacation Packages

Chicago Hotel Deals

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
111 W Huron St Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$2,744 per night from May 25 to May 26
NT$2,744
NT$4,228 total
May 25 - May 26
includes taxes & fees
8.2/10 Very Good! (2,689 reviews)
Place is in a great location but once you go past the lobby its very dated. Small rooms and had lots of trouble getting in touch with the front desk when we needed something.

Reviewed on 2026/5/7

Hotel Felix River North/Magnificent Mile
River Hotel

River Hotel

4 out of 5
75 East Wacker Drive Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,522 per night from May 25 to May 26
NT$4,522
NT$5,376 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (5,175 reviews)
Oh, River Hotel, how do I hate you? Let me count the ways. It was very difficult to find the hotel. It's narrow and short squished between two buildings which are much bigger. The hotels directions are terrible. All I have to say is that it's right next to the Sofitel, and I would've found it immediately. ...

Reviewed on 2026/5/7

River 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 NT$5,005 per night from May 27 to May 28
NT$5,005
NT$6,847 total
May 27 - May 28
includes taxes & fees
9.4/10 Exceptional! (4,080 reviews)
Centrally located hotel with breakfast included. Reasonable pricing for a new hotel. Recommended

Reviewed on 2026/5/7

Hotel Riu Plaza Chicago
See all 5,554 properties in Chicago
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

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.

Wrigley Field
Chicago Skyline, Chicago, Illinois shows amazing architecture in panoramic format

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.

Naval Base Great Lakes
Navy Pier

Navy Pier

4.5/5(4,925 reviews)

A ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.

Navy Pier

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