Central Chicago Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

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Top Central Chicago Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hotel Riu Plaza Chicago

Hotel Riu Plaza Chicago

4 out of 5
Downtown Chicago
Price was CA $1,067, price is now CA $747 per person
CA $747
per person
Jun 13 - Jun 15
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (3,688 reviews)
The room was clean. Very modern hotel. Great service and staff. Great experience overall.

Reviewed on Apr 7, 2026

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 CA $1,938, price is now CA $1,283 per person
CA $1,283
per person
Jun 18 - Jun 21
found 15 hours ago
Roundtrip non-stop flight included
Montreal (YMQ) to Chicago (ORD)
9.4/10 Exceptional! (2,401 reviews)
Everything was spectacular amenities,room,and customer service

Reviewed on Apr 6, 2026

The Langham, Chicago

The Langham, Chicago

5 out of 5
Downtown Chicago
Price was CA $4,255, price is now CA $2,858 per person
CA $2,858
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.8/10 Exceptional! (1,005 reviews)
The room was very clean, great location, and great staff.

Reviewed on Apr 6, 2026

Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

4.5 out of 5
Downtown Chicago
Price was CA $2,251, price is now CA $1,525 per person
CA $1,525
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
8.8/10 Excellent! (2,096 reviews)
It was too cold for the pool! The property is in a great location, the staff kind and very helpful. The on site restaurant is quite wonderful. I would have to say we had the best meal of our stay of 4 nights in Chicago!the rooms are large and airy and very clran

Reviewed on Apr 7, 2026

Viceroy Chicago

Viceroy Chicago

4.5 out of 5
Downtown Chicago
Price was CA $2,869, price is now CA $2,016 per person
CA $2,016
per person
May 20 - May 27
found 1 day ago
Roundtrip flight included
Toronto (YTZ) to Chicago (ORD)
9.4/10 Exceptional! (1,187 reviews)
Excellent choice for solo or business travelers looking for rooms with a good amount of space and a comfortable desk for working from. Great location.

Reviewed on Apr 6, 2026

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

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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 CA $151 per night from Apr 16 to Apr 17
CA $151
CA $177 total
Apr 16 - Apr 17
includes taxes & fees
8/10 Very Good! (10,052 reviews)
The hotel is very run down and smells as soon as you enter rooms are a great size and clean but very thin walls and you can hear everything called security on first night and took over an hr for someone to come no help at all never got any sleep that night all in all I would not stay here again much ...

Reviewed on Apr 7, 2026

Congress Plaza Hotel
Hilton Chicago/Magnificent Mile Suites

Hilton Chicago/Magnificent Mile Suites

3.5 out of 5
198 E Delaware Pl Chicago IL
Fully refundableReserve now, pay when you stay
The price is CA $191 per night from Apr 26 to Apr 27
CA $191
CA $224 total
Apr 26 - Apr 27
includes taxes & fees
9/10 Wonderful! (4,077 reviews)
Didn’t like the bed so much and the couch wasn’t comfy but overall I would stay again

Reviewed on Apr 7, 2026

Hilton Chicago/Magnificent Mile Suites
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St Chicago IL
The price is CA $193 per night from Apr 19 to Apr 20
CA $193
CA $226 total
Apr 19 - Apr 20
includes taxes & fees
8.6/10 Excellent! (5,833 reviews)
The pool was small and I felt like it was not clean. Kids couldn’t even see under water with their goggles. There were a lot of kids running around without parents and we had several knocks on our door from kids messing around. We did call down to the front desk and they sent security up immediately. ...

Reviewed on Apr 7, 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 1,452 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.
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Discover the most popular places to visit in Central Chicago

Navy Pier

Navy Pier

4.5/5(460 reviews)

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

4.5/5(20 reviews)

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

4.5/5(736 reviews)

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

Millennium Park

What to do in Central Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

CA $37
per adult
86% of travellers recommend
360 CHICAGO Observation Deck
Wendella's Lake and River Architecture Tour

Wendella's Lake and River Architecture Tour

CA $61
per adult
94% of travellers recommend
Wendella's Lake and River Architecture Tour
Flyover in Chicago

Flyover in Chicago

CA $52
per adult
98% of travellers recommend
Flyover in Chicago
See all activities in Central Chicago

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.