Central Chicago Vacations from NT$57,529

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The Latest Central Chicago Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Paxton Inn Motel

Paxton Inn Motel

2 out of 5
Price was NT$58,228, price is now NT$57,529 per person
NT$57,529
per person
Jul 6 - Jul 10
found 5 hours ago
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
6.4/10 (39 reviews)
Good location, room could have been cleaner

Reviewed on 2025/8/3

Cobblestone Hotel & Suites - Paxton

Cobblestone Hotel & Suites - Paxton

2.5 out of 5
Price was NT$63,041, price is now NT$61,602 per person
NT$61,602
per person
Jul 6 - Jul 10
found 5 hours ago
Roundtrip flight included
Taipei (TPE) to Chicago (ORD)
9.4/10 Exceptional! (494 reviews)
Breakfast was good the first morning but the second morning, everything was practically empty and didn’t get refilled until breakfast was almost over. We left hungry the second morning

Reviewed on 2026/4/26

Where to stay in Central Chicago

Find the best Central Chicago areas and neighborhoods for the activities you enjoy most. Learn more about Central Chicago
Magnificent Mile

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.

Find hotels in Magnificent Mile

Find the Best Central Chicago Vacation Packages

Central Chicago Hotel Deals

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
The price is NT$4,213 per night from May 26 to May 27
NT$4,213
NT$5,009 total
May 26 - May 27
includes taxes & fees
8/10 Very Good! (10,151 reviews)
"Always stay here when I’m trying to save money great location and price"

Reviewed on 2026/5/17

Congress Plaza 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$4,700 per night from May 25 to May 26
NT$4,700
NT$6,488 total
May 25 - May 26
includes taxes & fees
Hotel Riu Plaza Chicago
The Chicago Hotel Collection - Magnificent Mile

The Chicago Hotel Collection - Magnificent Mile

4 out of 5
166 E Superior Street Chicago IL
Fully refundable
The price is NT$3,830 per night from May 25 to May 26
NT$3,830
NT$4,554 total
May 25 - May 26
includes taxes & fees
7.8/10 Good! (1,430 reviews)
"The front desk staff at night and during the day upon checkout were incredibly warm, welcoming and friendly. Our original hotel was oversold and the front desk staff at that “unnamed” hotel just a few blocks away were awful and rude. It was a welcoming experience to come to this hotel and be greeted ..."

Reviewed on 2026/5/18

The Chicago Hotel Collection - Magnificent Mile
See all 1,477 properties in Central 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 Central Chicago

Navy Pier

Navy Pier

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

Navy Pier
Scene of Chicago street bridge with traffic among modern buildings of Downtown Chicago at Michigan avenue in Chicago, Illinois, United States, Business and Modern Transportation concept

Michigan Avenue

You can enjoy some retail therapy when you visit Michigan Avenue, a popular shopping spot in Chicago. Amble around this vibrant area's riverfront and enjoy its top-notch restaurants.

Michigan Avenue
Millennium Park

Millennium Park

A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.

Millennium Park

Frequently asked questions

Can I cancel my flight booking to Central Chicago due to COVID-19?
In these times of uncertainty, many airlines are offering more flexibility. Click through to our Customer Service Portal to find information about changing or canceling your booking due to COVID-19.
What's the best way to find cheap flights to Central Chicago that have flexible change policies?
Search for your low-cost flights to Central Chicago, then check the "No change fee" box below the "Flexible change policies" subheading. It really is that simple. We get that plans change and flexibility is important, so you can book with confidence with Expedia.
What are some of the general tips for travelers to Central Chicago during the COVID-19 outbreak?
COVID-19 has transformed the world in a profound way, including how we can travel safely. The following tips will help you navigate these new challenges and get you ready for your journey to Central Chicago:
  • Research if any travel restrictions apply to your destination and origin before booking your flight. Also check if there are any requirements you'll have to follow on arrival, such as health testing.
  • Requirements state that you must wear a face mask at the airport, including at security checkpoints. You should be prepared to lower your mask for ID purposes when asked by a TSA employee.
  • Avoid handing your boarding pass (electronic or paper) directly to a TSA officer. Instead, position the pass on the scanner and then hold it up for inspection.
  • You are now allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on luggage. You'll have to remove it for screening.
  • Empty your personal items from your pockets, like your wallet and phone, and put them in your carry-on instead of into bins. This will minimize handling during screening.
  • Transport all food items in a clear plastic bag and also put them in a screening bin. Separating food from your carry-on means it's less likely a TSA employee will need to open and touch your bag for inspection.

Which airlines fly to Central Chicago?
Arrange your ticket with American Airlines and then start piecing together your Central Chicago travel agenda. This leading airline runs 13307 flights every month to O'Hare Intl. Airport (ORD), a main gateway.
How can I find cheap tickets to Central Chicago?
In the last seven days, was the best price for a flight to Central Chicago. If you want to save even more, book well in advance and be flexible with your dates. Search for your trip to Central Chicago, then see prices for similar time frames by clicking on our "flexible dates" link.
How much is a flight to Central Chicago?
One-way flights from () sold for just in the last seven days. During this time, the price of a return ticket to Central Chicago varied between and . If you spot a bargain ticket, book as fast as you can — these prices don't hang about.
What are the most popular airports to fly into in Central Chicago?
Book your flight to O'Hare Intl. Airport (ORD) and sample the best that Central Chicago has to offer. As the region's main entry point, about 33491 flights land here every month.
When is the cheapest time to fly to Central Chicago?
If you'd rather spend your money enjoying Central Chicago rather than on getting there, depart early in the week. The cheapest day to fly is usually Tuesday, with Monday running a close second. With many folks keeping their travel to weekends, Saturday typically has the most expensive airfares.
How much is a plane ticket to Central Chicago?
Fares varied from to in the last seven days. When you're ready to book, we'll be ready to help you land a great deal to Central Chicago.
Which airlines with flights to Central Chicago employ COVID-19 cleanliness policies?
In response to the COVID-19 pandemic, many airlines have implemented extra rules and standards to help travelers fly with peace of mind. Here are some good examples:
  • United Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.
  • Delta - this airline is known for electrostatic cleaning and cleaning with disinfectant.

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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.