Central Chicago Holidays

Photo by Phil Ostroff

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Top Flight + Hotel Deals in Central Chicago

Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
Downtown Chicago
Price was €1,693, price is now €1,349 per person
€1,349
per person
23 Jun - 30 Jun
found 15 hours ago
Return flight included
Dublin (DUB) to Chicago (ORD)
8.6/10 Excellent! (5,808 reviews)
We’re very happy with our stays And definitely recommend and comeback

Reviewed on 11 Apr 2026

Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

5 out of 5
Downtown Chicago
Price was €3,471, price is now €2,546 per person
€2,546
per person
24 Jun - 30 Jun
found 17 hours ago
Return direct flight included
Johannesburg (JNB) to Chicago (ORD)
9.4/10 Exceptional! (1,848 reviews)
Beautiful facility, excellent service, professional staff, delicious food!

Reviewed on 7 Apr 2026

Level Chicago Fulton Market

Level Chicago Fulton Market

4 out of 5
Downtown Chicago
Price was €2,476, price is now €1,860 per person
€1,860
per person
24 Jun - 30 Jun
found 17 hours ago
Return direct flight included
Johannesburg (JNB) to Chicago (ORD)
9.2/10 Wonderful! (436 reviews)
Great location! Easy parking and the rooms were gorgeous! We will definitely stay here next time we visit Chicago

Reviewed on 10 Apr 2026

Sports Illustrated Resorts Chicago

Sports Illustrated Resorts Chicago

3.5 out of 5
Downtown Chicago
Price was €2,396, price is now €1,889 per person
€1,889
per person
24 Jun - 30 Jun
found 17 hours ago
Return direct flight included
Johannesburg (JNB) to Chicago (ORD)
9.2/10 Wonderful! (1,409 reviews)
Very friendly staff, great location.

Reviewed on 6 Apr 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Price was €2,130, price is now €1,701 per person
€1,701
per person
24 Jun - 30 Jun
found 17 hours ago
Return direct flight included
Johannesburg (JNB) to Chicago (ORD)
8.2/10 Very Good! (2,604 reviews)
Nice, but no microwave or refrigerator in room. Staff is nice and place was clean. Many things to do around.

Reviewed on 11 Apr 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

Shopaholics need look no further this glittering street packed with boutique and luxury shops, famous department stores and cafes.

Find hotels in Magnificent Mile

Top hotels in Central Chicago

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 €123 per night from 26 Apr to 27 Apr
€123
26 Apr - 27 Apr
includes taxes & fees
8/10 Very Good! (10,091 reviews)
.

Reviewed on 11 Apr 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 €137 per night from 26 Apr to 27 Apr
€137
26 Apr - 27 Apr
includes taxes & fees
9/10 Wonderful! (4,105 reviews)
Don’t book through Expedia, I had to leave my vacation early because I had to rush my travel companion to the ER as they were struggling to breathe. Great hotel, just don’t book through Expedia. You will have problems.

Reviewed on 11 Apr 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
Fully refundableReserve now, pay when you stay
The price is €156 per night from 19 Apr to 20 Apr
€156
19 Apr - 20 Apr
includes taxes & fees
8.6/10 Excellent! (5,841 reviews)
Definitely a family hotel! There were lots of other families there ranging in all ages. The pool is not that big but was nice to have. Be warned though the pool was very cold. Sometimes it was super busy and other times pretty open (we were there during spring break so I’m sure that played a part). ...

Reviewed on 11 Apr 2026

Embassy Suites by Hilton Chicago Downtown River North
See all 1,487 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.

Popular places to visit

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 find the perfect gifts to bring home 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

What to do in Central Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

€23
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

€35
per adult
94% of travellers recommend
Art Institute of Chicago
Wendella's 90-min Chicago River Architecture Tour

Wendella's 90-min Chicago River Architecture Tour

€35
per adult
94% of travellers recommend
Wendella's 90-min Chicago River Architecture Tour
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 cancelling 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 travellers 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 travellers 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.