Chicago Vacations from NT$19,850
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The Latest Chicago Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Freehand Chicago
Aug 27 - Aug 30Freehand Chicago + Flight
Downtown Chicago3 nights4.0 star property7.8/10 - Good (3,222 reviews)"Rooms good for sleeping. Not much room to move arround. City view through smaller windows. Beds are comfortable."Reviewed July 26, 2026Roundtrip • Detroit (DTW) - Chicago (ORD)DTW - ORD • Nonstop ORD - DTW • Nonstop - Hotel Felix River North/Magnificent Mile
Aug 27 - Aug 30Hotel Felix River North/Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.2/10 - Very Good (2,865 reviews)"Would not stay at this hotel ages"Reviewed July 26, 2026Roundtrip • Detroit (DTW) - Chicago (ORD)DTW - ORD • Nonstop ORD - DTW • Nonstop - Fairmont Chicago at Millennium Park
Aug 27 - Aug 30Fairmont Chicago at Millennium Park + Flight
Downtown Chicago3 nights4.5 star property8.8/10 - Excellent (2,271 reviews)"The hotel location and view from the room (we had city view) were great! The breakfast in Toro restaurant was delicious with some decent options for kids and reasonably priced. The only complaints were 1) no grab and go food options at around 2PM 2) the room service could have been better. We asked for fridge (the one in the room was not for personal use) which was delivered after 1 hr only. We have also asked for water which was not delivered until next day."Reviewed July 26, 2026Roundtrip • Detroit (DTW) - Chicago (ORD)DTW - ORD • Nonstop ORD - DTW • Nonstop - Chicago Marriott Downtown Magnificent Mile
Aug 27 - Aug 30Chicago Marriott Downtown Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property8.8/10 - Excellent (1,001 reviews)Roundtrip • Detroit (DTW) - Chicago (ORD)DTW - ORD • Nonstop ORD - DTW • Nonstop - Eurostars Magnificent Mile
Aug 27 - Aug 30Eurostars Magnificent Mile + Flight
Downtown Chicago3 nights4.0 star property9.0/10 - Wonderful (3,743 reviews)"El hotel súper céntrico, cerca de todo. Muchos lugares de comer a sus alrededores, el personal excelente y no se diga la habitación, cómoda siempre en orden y limpia. Fue más de lo que esperaba excelente hotel."Reviewed July 25, 2026Roundtrip • Detroit (DTW) - Chicago (ORD)DTW - ORD • Nonstop ORD - DTW • Nonstop
Where to stay in Chicago
Find the best Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Chicago
Learn more about Chicago
The Loop
Chicago's central business district boasts numerous global businesses, retail establishments, and theaters. Explore the Loop Retail Historic District, Chicago Landmark Historic Michigan Boulevard District, and visit iconic attractions like the Art Institute of Chicago.
Photo by Polina Quick
Open Photo by Polina Quick
Photo by throwingsofas
Open Photo by throwingsofas
Photo by Katie Robinson
Open Photo by Katie Robinson
River North
Artistic spirit thrives here, with art galleries and a design district featuring luxury interior furnishings. Explore Kingsbury Park, enjoy vibrant nightlife on Hubbard Street, and visit the iconic Contemporaine Building.
Photo by © City of Chicago
Open Photo by © City of Chicago
Magnificent Mile
Upscale shopping district with luxury department stores, boutiques, and acclaimed restaurants, featuring landmarks like the Wrigley Building and Chicago Water Tower. The Magnificent Mile is easily accessible by public transit and seasonal trolley service.
Photo by throwingsofas
Open Photo by throwingsofas
West Loop
West Loop has transformed from industrial roots into Chicago's trendiest food destination. Old warehouses now house sleek restaurants along "Restaurant Row" where celebrity chefs create culinary magic. Art galleries and design studios fill converted brick buildings throughout this vibrant neighborhood. Union Park and Mary Bartelme Park offer green retreats amid the urban landscape. Getting around is simple with multiple train stations including Racine and Clinton. The neighborhood balances its industrial heritage with modern luxury in this walkable food lover's paradise.
Lincoln Park
Upscale national retailers, boutiques, and bookstores abound in this affluent area, alongside numerous restaurants and coffee shops. Must-see attractions include Lincoln Park Zoo, Chicago History Museum, and North Avenue Beach. Easily accessible via CTA transit and major roads.
Discover the most popular places to visit in Chicago
Photo by © City of Chicago
Open Photo by © City of Chicago
Wrigley Field
9.0/10 (11,704 reviews)
Step into baseball's living museum where ivy-covered walls and a hand-operated scoreboard create timeless charm. Experience the electrifying atmosphere of Cubs games in this century-old "Friendly Confines."
Photo by © City of Chicago
Open Photo by © City of Chicago
Soldier Field
8.8/10 (7,063 reviews)
Soldier Field blends historic neoclassical columns with modern design as home to the Chicago Bears. Experience the electric atmosphere of an NFL game or take a guided tour exploring its century of sporting heritage.
Photo by © Cesar Russ Photography
Open Photo by © Cesar Russ Photography
McCormick Place
8.8/10 (9,822 reviews)
McCormick Place hosts major events like the Chicago Auto Show in its 2.6 million square feet of exhibition space. Arrive via the convenient Metra Electric Line station directly beneath the complex.
Chicago Hotel Deals
9.4 out of 10, Exceptional, (4,821 reviews)
9.4/10
Exceptional
(4,821 reviews)
"Great location right on the magnificent mile. Walking distance to Navy pier and millennium Park. Fantastic rooftop pair"
The price is NT$6,956
NT$6,956
NT$9,193 total
includes taxes & fees
Aug 23 - Aug 24
Hyatt Place Chicago/Downtown - The Loop
Hyatt Place Chicago/Downtown - The Loop3.0 star property
0.6 km from Chicago (and vicinity)
8.8 out of 10, Excellent, (1,469 reviews)
8.8/10
Excellent
(1,469 reviews)
The price is NT$6,540
NT$6,540
NT$7,775 total
includes taxes & fees
Aug 9 - Aug 10
9.4 out of 10, Exceptional, (3,499 reviews)
9.4/10
Exceptional
(3,499 reviews)
"Clean room friendly staff the Bell men were awesome 👌"
The price is NT$7,446
NT$7,446
NT$10,008 total
includes taxes & fees
Aug 9 - Aug 10
InterContinental Chicago Magnificent Mile by IHG
InterContinental Chicago Magnificent Mile by IHG4.5 star property
1.2 km from Chicago (and vicinity)
9.2 out of 10, Wonderful, (3,166 reviews)
9.2/10
Wonderful
(3,166 reviews)
The price is NT$7,222
NT$7,222
NT$9,719 total
includes taxes & fees
Aug 9 - Aug 10
Courtyard by Marriott Chicago Magnificent Mile
Courtyard by Marriott Chicago Magnificent Mile3.0 star property
1.5 km from Chicago (and vicinity)
9.0 out of 10, Wonderful, (1,990 reviews)
9.0/10
Wonderful
(1,990 reviews)
The price is NT$6,961
NT$6,961
NT$8,276 total
includes taxes & fees
Aug 16 - Aug 17
Hilton Chicago/Magnificent Mile Suites
Hilton Chicago/Magnificent Mile Suites3.5 star property
2.2 km from Chicago (and vicinity)
9.0 out of 10, Wonderful, (4,650 reviews)
9.0/10
Wonderful
(4,650 reviews)
"When we arrive the Fridge was not working and smelled like old food. It took the staff a couple hours to get it replaced."
The price is NT$6,076
NT$6,076
NT$7,225 total
includes taxes & fees
Aug 16 - Aug 17
La Quinta Inn & Suites by Wyndham Chicago Downtown
La Quinta Inn & Suites by Wyndham Chicago Downtown3.0 star property
0.6 km from Chicago (and vicinity)
8.6 out of 10, Excellent, (2,832 reviews)
8.6/10
Excellent
(2,832 reviews)
"I was reservation a room for 3 peoples, when we arrived that night only 1 blanket in the room, I call to the front desk and she said we sold out and no more blankets, I can't believe she said that and hang up, I call back and no one pick up the phone."
The price is NT$5,769
NT$5,769
NT$7,436 total
includes taxes & fees
Aug 9 - Aug 10
Aloft by Marriott Chicago Mag Mile
Aloft by Marriott Chicago Mag Mile3.0 star property
1.5 km from Chicago (and vicinity)
8.6 out of 10, Excellent, (3,320 reviews)
8.6/10
Excellent
(3,320 reviews)
The price is NT$6,054
NT$6,054
NT$7,198 total
includes taxes & fees
Aug 9 - Aug 10
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.
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.