Central Chicago Vacations from $823
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The Latest Central Chicago vacation packages
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $1,291, price is now $823 per person
$823
per person
Aug 19 - Aug 23
found 1 day ago
Roundtrip flight included
Boston (BOS) to Chicago (ORD)
9/10 Wonderful! (478 reviews)
Staff was amazing and the apartment building was phenomenally clean!
Reviewed on May 28, 2026
Hotel Riu Plaza Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,394, price is now $916 per person
$916
per person
Jun 30 - Jul 5
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (4,188 reviews)
Hotel room was very neat and clean. The continental breakfast on the second floor was fantastic and had a vast variety of breakfast food to choose from. For the amount of food and people for this room, the staff did an excellent job keeping this cleaned and very well maintained. Upon checking in and checking out, the staff was very warm and friendly. The customer service was top-notch. Would recommend to anyone staying in Chicago to stay here!
Reviewed on May 30, 2026
Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,804, price is now $1,194 per person
$1,194
per person
Jun 30 - Jul 5
found 2 days ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (2,511 reviews)
Without a doubt, the view of the pier and city skyline was the BEST part of this hotel experience. The room was pretty large and had a great sitting area to read, gaze at the water, people watch, and relax. The hotel staff was nice and helpful. Everything I needed and wanted to do for this trip was at the Navy Pier so the Sable Hotel checked all my boxes.
Reviewed on May 28, 2026
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,954, price is now $1,371 per person
$1,371
per person
Jul 9 - Jul 12
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,001 reviews)
Our third time at this hotel and still enjoying it.
Reviewed on May 30, 2026
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all tripsWhere 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
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.
Discover the most popular places to visit in Central Chicago
Michigan Avenue
4.5/5(336 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.
Navy Pier
4.5/5(4,925 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
Millennium Park
4.5/5(7,309 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
What to do in Central Chicago
Skydeck - Willis Tower Admission
$44
per adult
96% of travellers recommend
Central Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$140 nightly
The price is $166 total per night from Jun 29 to Jun 30
$166 total
Jun 29 - Jun 30
Total with taxes and fees
8/10 Very Good! (10,135 reviews)
"The room was small and was missing modern convinces-microwave-better seating space. The staff were friendly and the restaurant was great! I only wished we had gotten a better room! Special shout out to Steve P. the doorman for his service and friendly demeanor!!"
Reviewed on May 30, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$203 nightly
The price is $242 total per night from Jun 30 to Jul 1
$242 total
Jun 30 - Jul 1
Total with taxes and fees
9.4/10 Exceptional! (4,301 reviews)
"Clean"
Reviewed on May 31, 2026
The Chicago Hotel Collection - Magnificent Mile
166 E Superior Street Chicago IL
Fully refundable
$154 nightly
The price is $183 total per night from Jun 14 to Jun 15
$183 total
Jun 14 - Jun 15
Total with taxes and fees
7.8/10 Good! (1,493 reviews)
"Asked for a room with a tub didn't get it and got extra charges after stay. Got my full deposit back but got extra charges. And paid for breakfast after being told it was included. No cable on tv"
Reviewed on May 30, 2026
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.
Find the Best Central Chicago Vacation Packages
Central Chicago Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | O'Hare Intl. Airport (ORD) |
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- Chicago Vacations
- Visit Downtown Chicago
- Navy Pier
- Chicago Riverwalk
- Chicago Theatre
- Wrigley Building
- Tribune Tower
- Michigan Avenue Bridge
- Marina City
- Visit Chicago
- Shops at North Bridge
- Museum of Broadcast Communications
- Michigan Avenue
- American Medical Association Headquarters
- Carbide and Carbon Building
- House of Blues Chicago
- Ronald McDonald House near Lurie Children’s
- Downtown Chicago Vacations
- Where to stay in Chicago
- Daley Plaza
- Millennium Park
- Chinese Consulate
- Driehaus Museum
- Aon Center
- Magnificent Mile Vacations
- Water Tower Place
- Ohio Street Beach
- Streeterville Vacations
- Goodman Theater
- St. James Cathedral
- Marshall Field Building
- Chicago Water Tower
- Chicago Cultural Center
- Noble Fool Theater
- 875 North Michigan Avenue
- Chicago Place Mall
- The Loop Vacations
- Northwestern Memorial Hospital
- Holy Name Cathedral
- Cloud Gate
- Visit The Loop
- Harris Theater
- Picasso Statue
- Willis Tower
- Art Institute of Chicago
- Richard J. Daley Center
- Richard Norton Gallery
- Chase Tower
- Milton Lee Olive Park
- Cadillac Palace Theatre
- Merchandise Mart
- Chicago City Hall
- Miró's Chicago
- Ann and Robert H. Lurie Children's Hospital
- Chicago Temple
- Prentice Women's Hospital
- State Street
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
