Central Chicago Holidays

Photo by Phil Ostroff

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Central Chicago Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn & Suites Chicago - Downtown by IHG

Holiday Inn & Suites Chicago - Downtown by IHG

3 out of 5
Downtown Chicago
Price was S$1,114, price is now S$897 per person
S$897
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (1,008 reviews)
Comfortable bed but very basic hotel. Not as expected for the amount we paid.

Reviewed on 26 Apr, 2026

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,477, price is now S$899 per person
S$899
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.8/10 Excellent! (2,168 reviews)
The hotel’s location is fantastic, putting you within walking distance of some great eats. Don't miss the rooftop bar; it has a cool indoor-outdoor setup that stays busy with locals and guests alike. It’s a bit of a splurge for drinks, but the atmosphere makes up for it. The rooms are a highlight—very modern and beautiful with great city views. As for the service, the staff was friendly and capable, though they felt a bit "all business" rather than warm. Definitely a comfortable place to call home for a few days.

Reviewed on 24 Apr, 2026

Hotel Felix River North/Magnificent Mile

Hotel Felix River North/Magnificent Mile

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was S$1,398, price is now S$970 per person
S$970
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.2/10 Very Good! (2,636 reviews)
Great location and value

Reviewed on 25 Apr, 2026

Warwick Allerton - Chicago

Warwick Allerton - Chicago

4 out of 5
Downtown Chicago
Price was S$1,202, price is now S$922 per person
S$922
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
8.6/10 Excellent! (3,051 reviews)
It was great! Place was clean! Lobby was beautiful! The beds were a bit hard, kind of like sleeping on a wooden box but that doesn’t deter your stay, and the staff were accommodating! If you want to do an early check in, best to do it at 2pm, anything earlier, you’ll have to pay! You can also store your luggage while waiting for your check in

Reviewed on 26 Apr, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was S$1,432, price is now S$1,124 per person
S$1,124
per person
5 Jun - 7 Jun
found 1 day ago
Return flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (3,280 reviews)
Really good spot and location. Staff was super helpful and nice.

Reviewed on 22 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

A dazzling array of boutiques, luxury shops, famous department stores and pleasant cafés, where shopaholics can lose themselves for hours.

Find hotels in Magnificent Mile

Top hotels in Central Chicago

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 S$169 per night from 28 Apr to 29 Apr
S$169
28 Apr - 29 Apr
includes taxes & fees
8.2/10 Very Good! (2,643 reviews)
Staff was so kind and great!

Reviewed on 26 Apr, 2026

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 S$179 per night from 25 May to 26 May
S$179
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (5,131 reviews)
I have stayed at the River Hotel multiple times and never been disappointed. Its convenient location downtown, clean rooms, and helpful staff work well for the business trips I take to Chicago.

Reviewed on 26 Apr, 2026

River Hotel
Club Quarters Hotel, Central Loop, Chicago

Club Quarters Hotel, Central Loop, Chicago

4 out of 5
111 West Adams Street Chicago IL
Fully refundableReserve now, pay when you stay
The price is S$166 per night from 25 May to 26 May
S$166
25 May - 26 May
includes taxes & fees
8.8/10 Excellent! (3,464 reviews)
I was only in town for one day. But it was an easy seamless check-in. The room was clean and bathroom was clean. Everything in the room work and I had no need to call or any assistance. The checkout was very simple was done on my phone as I walk down the hallway before leaving.

Reviewed on 26 Apr, 2026

Club Quarters Hotel, Central Loop, Chicago
See all 1,498 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

McCormick Place

McCormick Place

Attend an event at the United States’ largest convention center, which features hyper-modern facilities and huge exhibition spaces connected by promenades and sky bridges.

McCormick Place
Millennium Park

Millennium Park

One of Chicago’s main focal points, where locals and visitors flock to see the striking art, architecture and landscape on show.

Millennium Park
Soldier Field

Soldier Field

Events center, NFL stadium and historic landmark all in one, this waterfront field is one of Chicago’s most popular destinations.

Soldier Field

What to do in Central Chicago

360 CHICAGO Observation Deck

360 CHICAGO Observation Deck

S$34
per adult
88% of travellers recommend
360 CHICAGO Observation Deck
Art Institute of Chicago

Art Institute of Chicago

S$51
per adult
92% of travellers recommend
Art Institute of Chicago
Skydeck - Willis Tower Admission

Skydeck - Willis Tower Admission

S$56
per adult
96% of travellers recommend
Skydeck - Willis Tower Admission
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.