Central Chicago Vacations from $242
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The Latest Central Chicago vacation packages
Price found within the past 48 hours. Click for updated prices.
The Emily Hotel
Downtown Chicago
Save 100% on your flight
Price was $799, price is now $435 per person
$435
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,248 reviews)
Small, but adequate room. Was there for a wedding on property. Suggestion: blankets?
Reviewed on Nov 10, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $823, price is now $455 per person
$455
per person
Dec 18 - Dec 23
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
Property was clean, centrally located with wonderful staff. Will definitely stay again.
Reviewed on Nov 9, 2025
Hotel Versey Chicago Lincoln Park
Lakeview
Save 100% on your flight
Price was $705, price is now $395 per person
$395
per person
Dec 23 - Dec 30
found 17 hours ago
Roundtrip flight included
Dallas (DFW) to Chicago (ORD)
8.6/10 Excellent! (1,488 reviews)
Very good place to stay to see a hockey game
Reviewed on Nov 6, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $543, price is now $305 per person
$305
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,110 reviews)
Rooms are lovely, bar / restaurant is top notch. Love staying at the pendry!
Reviewed on Nov 10, 2025
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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(332 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.
Millennium Park
4.5/5(7,198 reviews)
A landmark gathering place for locals and visitors who come to admire the unique art, architecture and landscape.
Navy Pier
4.5/5(4,870 reviews)
A Ferris wheel, shopping, restaurants and more can be found in this waterfront entertainment district.
What to do in Central Chicago
Skydeck - Willis Tower Admission
$44
per adult
98% of travellers recommend
Chicago: Navy Pier Centennial Wheel Ticket
$25
per adult
84% of travellers recommend
Central Chicago Hotel Deals
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$102 nightly
The price is $119 total per night from Dec 8 to Dec 9
$119 total
Dec 8 - Dec 9
Total with taxes and fees
8.4/10 Very Good! (5,208 reviews)
Friendly staff, well appointed room, needed more pillows and received very quickly.
Reviewed on Nov 8, 2025
Hilton Chicago/Magnificent Mile Suites
198 E Delaware Pl, Chicago, IL
Fully refundableReserve now, pay when you stay
$101 nightly
The price is $119 total per night from Dec 7 to Dec 8
$119 total
Dec 7 - Dec 8
Total with taxes and fees
8.8/10 Excellent! (3,258 reviews)
Room was terrific; staff, very helpful. All in all a great trip, and I’ll definitely revisit this property.
Reviewed on Nov 10, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $129 total per night from Nov 20 to Nov 21
$129 total
Nov 20 - Nov 21
Total with taxes and fees
8/10 Very Good! (9,545 reviews)
It was fine in general. Location was great but view was not perfect just fine
Reviewed on Nov 9, 2025
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.
