Central Chicago Adventure Vacations
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Top Adventure vacation packages in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $645, price is now $423 per person
$423
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue.
However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic).
Reviewed on Oct 22, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,117, price is now $680 per person
$680
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $656 per person
$656
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,357, price is now $876 per person
$876
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
We had a devastating family emergency and the staff handled everything for us. They were so kind and compassionate. I don’t know how I could have handled getting to the airport and returning the rental car without them.
Reviewed on Oct 23, 2025
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See all available trips from Columbus to Central Chicago
View all trips5* Adventure vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $656 per person
$656
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,117, price is now $680 per person
$680
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Waldorf Astoria Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,357, price is now $876 per person
$876
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,004 reviews)
We had a devastating family emergency and the staff handled everything for us. They were so kind and compassionate. I don’t know how I could have handled getting to the airport and returning the rental car without them.
Reviewed on Oct 23, 2025
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips3 Night Adventure vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
Trump International Hotel & Tower Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,117, price is now $680 per person
$680
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.4/10 Exceptional! (1,761 reviews)
The kitchen was VERY clean and very well stocked. Our room was as nice as any room as I have ever stayed in. The Hotel Manager and Pablo, the Director of Rooms, were outstanding!!! they were truly a credit to the Trump brand. I have stayed at the Trump International and would stay there again in a heartbeat.
Reviewed on Oct 20, 2025
Park Hyatt Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,039, price is now $656 per person
$656
per person
Dec 26 - Dec 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9.6/10 Exceptional! (1,006 reviews)
This is a beautiful hotel with lots of amenities that feel kind of luxurious. We especially loved the huge tub in our room. Also, the staff was amazing. One gripe we had is that we paid quite a bit more for a lake view room and we were on the eighth floor, which did not really afford much of a view. We called the front desk to see if we could get a higher floor and they said there was nothing available, but they did bring us a bottle of wine to compensate. I know someone has to be on the lower floors, but it seems that if you are going to pay more for a view they should make sure you are on a higher floor. Other than that, we would definitely stay here again and would recommend!
Reviewed on Oct 20, 2025
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all trips4 Night Adventure vacations in Central Chicago
Price found within the past 48 hours. Click for updated prices.
The Blackstone, Autograph Collection
Downtown Chicago
Save 100% on your flight
Price was $467, price is now $248 per person
$248
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (1,003 reviews)
Fabulous hotel we will be back
Reviewed on Oct 20, 2025
Level Chicago – Old Town
Downtown Chicago
Save 100% on your flight
Price was $640, price is now $335 per person
$335
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
9/10 Wonderful! (367 reviews)
We booked a two-bedroom corner suite which was very spacious (especially the kitchen/living room area), and we had very good view of the old town overlooking from the big porch. The location of the hotel was pretty nice, only 15 min to Michigan Avenue.
However, a few things were disappointing: 1) The check-in process was longer than expected which took 15-20 min to get the room keys; 2) The floor of the suite was quite dusty and the door of the master bedroom was broken (could not be locked); 3) The room phone didn't work at all and we had to use our phone to call the hotel front desk to ask questions; 4) This was the one and only hotel we'd stayed worldwide that did not provide foam pillows (feather pillows only to which one of our family members was allergic).
Reviewed on Oct 22, 2025
Don't see what you're looking for?
See all available trips from Columbus to Central Chicago
View all tripsFind awesome Central Chicago adventure vacations
How can I book the best Central Chicago adventure trips?
Choose your own adventure in Central Chicago, whether that’s a white-knuckle experience or a weekend walk. Read the reviews of the adventures that have gone before to be sure your chosen stay is your idea of fun.
How can I plan the perfect Central Chicago family adventure vacation?
Adventure awaits when you select the family-friendly filter. There ’s plenty of excitement for all ages in Central Chicago. Just make sure to check your chosen escapade is within the realms of can-do for the whole clan and will have the whole team grinning.
Can I book all-inclusive Central Chicago adventure vacation packages?
By refining your filters, you can explore all-amazing, all-adventurous, all-inclusive vacation packages. Amp up the extravagance with a few more filters too. Pick pristine pools, sensational spas, or wondrous waterparks for a sensational adventure getaway.
Why should I book a Central Chicago adventure vacation for couples?
Book a Central Chicago couples adventure vacation for the ultimate in romance and memory-making. Stunning scenery, heart-racing happenings, and the grandeur of the great outdoors—it’s the best way to bond.
How can I find the best deals on adventure packages in Central Chicago?
It’s easy to unleash fabulously affordable adventures. Enter the dates for your caper, then sort your search results by price or deals.
Can I book an adventure vacation package in Central Chicago with free cancellation and/or flexible dates?
Yes! When you’re searching for a great getaway, filter by payment option for free cancellation, so a change of plans won’t mess up your adventures. You’ll find buy now, pay later options, too, for full-on flexibility.
Why should I book a Central Chicago adventure trip with Expedia?
Adventure, airfare, accommodation, ATOL protection, and activities—all on one site. And that’s just the benefits that begin with A.
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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.
