Chicago Adventure Vacation Packages
Best Chicago Adventure packages
Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
per person
Jun 30 - Jul 3
found 12 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Our favorite Chicago hotel. The location is perfect for exploring the city, dining, and walking. My only complaint is that the condition of the pool was not nearly as clean and clear as usual.
Reviewed on Jun 24, 2025
The Westin Chicago River North
Downtown Chicago
per person
Jun 30 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Asheville (AVL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), 24-hour room service, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
My kids had a women sneak onto the elevator and follow them to their room. Thankfully there were adults with them but she definitely had singled them out.
Reviewed on Mar 20, 2025
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 4
found 14 hours ago
Roundtrip flight included
Albuquerque (ABQ) 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.
Perfect property, everything is walkable distance
Reviewed on Jun 26, 2025
3 night Chicago Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Congress Plaza Hotel
Downtown Chicago
per person
Aug 31 - Sep 3
found 20 hours ago
Roundtrip flight included
Columbus (CMH) 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
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Aug 2 - Aug 5
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Perfect property, everything is walkable distance
Reviewed on Jun 26, 2025
The Westin Chicago River North
Downtown Chicago
per person
Jun 30 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Asheville (AVL) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy breakfast (surcharge), 24-hour room service, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
My kids had a women sneak onto the elevator and follow them to their room. Thankfully there were adults with them but she definitely had singled them out.
Reviewed on Mar 20, 2025
4 night Chicago Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
per person
Jun 30 - Jul 4
found 17 hours ago
Roundtrip non-stop flight included
Boston (BOS) 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.
Clean and attentive staff
Reviewed on Jun 21, 2025
Kinzie Hotel
Downtown Chicago
Save 100% on your flight
per person
Aug 3 - Aug 7
found 11 hours ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy room service, a fitness center, and valet parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Liked everything about this hotel and have stayed here a few times. Wish the gym was a little more up to date.
Reviewed on May 27, 2025
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Jul 31 - Aug 4
found 14 hours ago
Roundtrip flight included
Albuquerque (ABQ) 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.
Perfect property, everything is walkable distance
Reviewed on Jun 26, 2025
5 night Chicago Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
per person
Aug 31 - Sep 5
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Clean and attentive staff
Reviewed on Jun 21, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Aug 31 - Sep 5
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) 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
Embassy Suites by Hilton Chicago Downtown River North
Downtown Chicago
Save 100% on your flight
per person
Aug 31 - Sep 5
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Perfect property, everything is walkable distance
Reviewed on Jun 26, 2025
vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
Silversmith Hotel Chicago Downtown
Downtown Chicago
Save 100% on your flight
per person
Sep 12 - Sep 18
found 18 hours ago
Roundtrip flight included
Pittsburgh (PIT) to Chicago (ORD)
Stay at this 4-star business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Millennium Park and Art Institute of Chicago are located nearby.
One of my favorite places to stay in Chicago. Quiet, centrally located. Friendly, helpful staff.
Reviewed on Nov 10, 2024
Swissotel - Chicago
Downtown Chicago
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Ciudad Juarez (CJS) 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.
Clean and attentive staff
Reviewed on Jun 21, 2025
Pendry Chicago
Downtown Chicago
per person
Sep 1 - Sep 7
found 1 day ago
Roundtrip non-stop flight included
Ciudad Juarez (CJS) 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
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.
BWI
Baltimore Washington Intl. Thurgood Marshall
MDW
Midway Intl.
$76 Roundtrip, found 19 hours ago
$76
Roundtrip
found 19 hours ago
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$80 Roundtrip, found 8 hours ago
$80
Roundtrip
found 8 hours ago
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$83 Roundtrip, found 8 hours ago
$83
Roundtrip
found 8 hours ago
BWI
Baltimore Washington Intl. Thurgood Marshall
ORD
O'Hare Intl.
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$88 Roundtrip, found 2 hours ago
$88
Roundtrip
found 2 hours ago
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$88 Roundtrip, found 5 hours ago
$88
Roundtrip
found 5 hours ago
DAL
Love Field
MDW
Midway Intl.
$157 Roundtrip, found 4 days ago
$157
Roundtrip
found 4 days 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