Central Chicago Vacations from $367
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The Latest Central Chicago vacation packages
Price found within the past 48 hours. Click for updated prices.
Harrah's Joliet Casino & Hotel - A Caesars Rewards Destination
Price was $750, price is now $415 per person
$415
per person
Apr 30 - May 3
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.4/10 Very Good! (999 reviews)
Enjoyed the room. The staff could use a hug not the friendliest. The games our outdated. Seen many guest besides me decide to go play at the other area casino
Reviewed on Jan 1, 2026
La Banque Hotel
Price was $688, price is now $395 per person
$395
per person
Apr 23 - Apr 27
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
9.4/10 Exceptional! (447 reviews)
Courteous Staff, clean, one of the most beautiful and interesting hotel. The history is amazing. The restaurant is delicious and the community is outstanding. Plan to return in the spring.
Reviewed on Jan 26, 2026
Level Chicago – Old Town
Downtown Chicago
Price was $862, price is now $504 per person
$504
per person
May 8 - May 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (380 reviews)
My girlfriend and I had an awesome time enjoying the space for a fun girls night out. Would recommend to anyone!
Reviewed on Feb 2, 2026
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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
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
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.
Millennium Park
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Navy Pier
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Central Chicago
Chicago Bulls Basketball Game at United Center
$166
per adult
80% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
88% of travellers recommend
Chicago River: 1.5-Hour Guided Architecture Cruise
$44
per adult
98% of travellers recommend
Central Chicago Hotel Deals
Congress Plaza Hotel
520 South Michigan Avenue Chicago IL
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $109 total per night from Feb 16 to Feb 17
$109 total
Feb 16 - Feb 17
Total with taxes and fees
8/10 Very Good! (9,880 reviews)
Overall pretty great other than no microwave
Reviewed on Feb 15, 2026
Hotel Riu Plaza Chicago
150 East Ontario Street Chicago IL
Fully refundableReserve now, pay when you stay
$137 nightly
The price is $161 total per night from Feb 16 to Feb 17
$161 total
Feb 16 - Feb 17
Total with taxes and fees
9.2/10 Wonderful! (3,343 reviews)
Rooms were great and breakfast was delicious
Reviewed on Feb 14, 2026
Hilton Chicago
720 S Michigan Ave Chicago IL
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $192 total per night from Feb 27 to Feb 28
$192 total
Feb 27 - Feb 28
Total with taxes and fees
8.4/10 Very Good! (2,614 reviews)
Outdated rooms and our heater stopped working overnight and the temp fell to 60's which felt freezing given it was zero outside with snow flurries But Matt the maintenance guy came quickly at 6 am thankfully and got it back up and running. Other than that, a truly beautiful hotel and the restaurant ...
Reviewed on Feb 8, 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
- John Hancock Center
- 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.
