Chicago Adventure Vacation Packages
Best Chicago Adventure packages
Price found within the past 48 hours. Click for updated prices.
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4-star hotel in Chicago. Enjoy free breakfast, room service, and a fitness center. Our guests praise the breakfast and the pool in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Excellent stay. Room was clean and well-designed for our family. Fantastic complimentary breakfast every morning.
Reviewed on Jun 13, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry was historic and great
Reviewed on Jul 5, 2024
Hilton Chicago/Magnificent Mile Suites
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 23
found 1 day ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy a fitness center, valet parking (surcharge), and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Convenience, close to shops, restaurants, etc.
Reviewed on Jun 13, 2025
3 night Chicago Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 23
found 9 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Amazing hotel. My wife and I love staying here.
Reviewed on May 28, 2025
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 23
found 9 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Book a stay at this eco-certified hotel in Chicago. Enjoy 2 bars/lounges, breakfast (surcharge), and 24-hour room service. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Absolutely everybody and everything was "top"
Reviewed on May 27, 2025
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 23
found 9 hours ago
Roundtrip flight included
New York (LGA) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The location was perfect, we were able to do all that we had planned to over the course of the two days, and we enjoyed how walkable the area was.
Reviewed on Mar 5, 2025
4 night Chicago Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 24
found 12 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
It’s was easy- we were in our rooms within a Few minutes of arriving
Reviewed on Jun 1, 2025
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 24
found 12 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Amazing hotel. My wife and I love staying here.
Reviewed on May 28, 2025
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 24
found 12 hours ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the pool and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The location was perfect, we were able to do all that we had planned to over the course of the two days, and we enjoyed how walkable the area was.
Reviewed on Mar 5, 2025
5 night Chicago Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
Downtown Chicago
Save 100% on your flight
per person
Jul 20 - Jul 25
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
It’s was easy- we were in our rooms within a Few minutes of arriving
Reviewed on Jun 1, 2025
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 25
found 12 hours ago
Roundtrip flight included
Bozeman (BZN) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The staff were highly accommodating, and helped make the stay remarkably comfortable.
We were traveling with children under the age of 10, so having a restaurant option at the location (River North) was really great, but even more outstanding was the quality of the food! We are looking forward to a return trip soon!
Reviewed on Dec 9, 2024
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 25
found 12 hours ago
Roundtrip flight included
Bozeman (BZN) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Pendry was historic and great
Reviewed on Jul 5, 2024
vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 27
found 10 hours ago
Roundtrip flight included
Dallas (DAL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Grant Park and Millennium Park are located nearby.
It’s was easy- we were in our rooms within a Few minutes of arriving
Reviewed on Jun 1, 2025
The Royal Sonesta Chicago River North
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a 24-hour fitness center, and valet parking (surcharge). Our guests praise the pool and the restaurant in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The staff were highly accommodating, and helped make the stay remarkably comfortable.
We were traveling with children under the age of 10, so having a restaurant option at the location (River North) was really great, but even more outstanding was the quality of the food! We are looking forward to a return trip soon!
Reviewed on Dec 9, 2024
Palmer House a Hilton Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, breakfast (surcharge), and a 24-hour health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
Amazing hotel. My wife and I love staying here.
Reviewed on May 28, 2025
Adventure hotels in Chicago
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
Guests of Palmer House a Hilton Hotel enjoy a full-service spa, an indoor pool, and a 24-hour gym. Parking is available for USD 57 per night (USD 85 per night for valet parking), and there's also limo/town car service. Multilingual staff at the front desk are standing by 24/7 to help with access to locker space, securing valuables, and luggage storage. Other amenities at this spa hotel include a conference center, a business center, and express check-in.
Pool
Spa
Hyatt Regency McCormick Place Chicago
2233 S Martin Luther King Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
Guests of Hyatt Regency McCormick Place Chicago have access to an indoor pool, a gym, and a sauna. Parking is available for USD 40 per night (USD 60 per day for valet parking), and there's also a free casino shuttle. Multilingual staff at the 24-hour front desk can assist with securing valuables, dry cleaning/laundry, and tours or tickets. Additional amenities include free WiFi in public areas, meeting rooms, and a conference center.
Pool
Free WiFi
Hyatt Regency Chicago
151 East Wacker Dr, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
Guests of Hyatt Regency Chicago enjoy a gym, free WiFi in public areas, and meeting rooms. Valet parking is offered for USD 87 per night. The 24-hour front desk has multilingual staff ready to assist with tours or tickets, luggage storage, and dry cleaning/laundry. Additional amenities include conference space, a business center, and express check-in.
Free WiFi
Restaurant
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.
How much does it cost to fly to Chicago?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$87 Roundtrip, just found
$87
Roundtrip
just found
LGA
LaGuardia
ORD
O'Hare Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
LGA
LaGuardia
ORD
O'Hare Intl.
$97 Roundtrip, found 3 days ago
$97
Roundtrip
found 3 days ago
LGA
LaGuardia
MDW
Midway Intl.
$99 Roundtrip, found 3 days ago
$99
Roundtrip
found 3 days ago
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$123 Roundtrip, found 18 hours ago
$123
Roundtrip
found 18 hours ago
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$159 Roundtrip, found 4 days ago
$159
Roundtrip
found 4 days ago
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 1 hour ago
$197
Roundtrip
found 1 hour ago
Hotel themes
- Hotels with WiFi in Chicago
- Kid Friendly Hotels in Chicago
- Hotels with Restaurants in Chicago
- Business Hotels in Chicago
- Hotels with a Gym in Chicago
- Hotels with Free Parking in Chicago
- Hotels with Bar in Chicago
- Hotels with Free Breakfast in Chicago
- Hotels with Pool in Chicago
- Cheap Hotels in Chicago