Countryside Vacations from $358
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The Latest Countryside vacation packages
Price found within the past 48 hours. Click for updated prices.
Hotel Felix River North/Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $626, price is now $358 per person
$358
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
8.2/10 Very Good! (2,061 reviews)
Amazing service and friendly staff! Great place and within walkable distances to near by shops.
Reviewed on Aug 23, 2025
The Emily Hotel
Downtown Chicago
Price was $1,752, price is now $862 per person
$862
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.2/10 Wonderful! (1,182 reviews)
The staff here are absolutely the most helpful and sweetest. The hotel is perfect for a boutique hotel. The night life seemed to quite popular as well and right around Fulton market! I definitely recommend.
Also the coffee bags ? PERFECTION. Just had to add that
Reviewed on Aug 22, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Price was $2,180, price is now $1,157 per person
$1,157
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,690 reviews)
This property is beautiful and located in a great area.
Reviewed on Aug 19, 2025
The Langham, Chicago
Downtown Chicago
Price was $3,789, price is now $2,161 per person
$2,161
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.8/10 Exceptional! (1,003 reviews)
Phenomenal service. Exactly how a 5* hotel should be run. Everything was perfect.
Reviewed on Aug 12, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
Price was $1,030, price is now $596 per person
$596
per person
Nov 10 - Nov 16
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,005 reviews)
A beautiful step back in time with modern amenities. Amazing staff and easy access to anything you want to do in the city.
Reviewed on Aug 21, 2025
Don't see what you're looking for?
See all available trips from Columbus to Countryside
View all tripsDiscover the most popular places to visit in Countryside
Wrigley Field
4.5/5(2,128 reviews)
Tour the iconic grounds and catch a game March through September at Chicago’s beloved baseball stadium.
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.
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 Countryside
Wendella's 90-min Chicago River Architecture Tour
$41
per adult
94% of travellers recommend
Chicago By Night River & Lake Cruise
$45
per adult
96% of travellers recommend
Countryside Hotel Deals
The Wade
644 N Lake Shore Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $177 total per night from Sep 1 to Sep 2
$177 total
Sep 1 - Sep 2
Total with taxes and fees
8.2/10 Very Good! (1,218 reviews)
"Friendly"
Reviewed on Aug 24, 2025
Congress Plaza Hotel
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
$153 nightly
The price is $180 total per night from Sep 1 to Sep 2
$180 total
Sep 1 - Sep 2
Total with taxes and fees
7.8/10 Good! (8,996 reviews)
Great view! Safe location for food music and park
"Got a very good rate during an event that had filled up many nearby hotels. Lovely sparkling-clean room, rather small, a firm king bed, dresser, & table. It felt cozy, not crowded, enough drawers and closet space, nice-size bathroom with shower-tub. Room has nice ornate details. 10th-floor sunrise ..."
Reviewed on Aug 24, 2025
Embassy Suites by Hilton Chicago Downtown River North
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
$152 nightly
The price is $179 total per night from Sep 3 to Sep 4
$179 total
Sep 3 - Sep 4
Total with taxes and fees
8.4/10 Very Good! (4,765 reviews)
"Everyone was very helpful and polite. The room was clean and spacious. My kids loved the breakfast and snacks at night."
Reviewed on Aug 23, 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.
More vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.