Illinois Adventure Vacation Packages
Best Illinois Adventure packages
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!
Reviewed on Jun 15, 2025
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Sep 1 - Sep 4
found 1 day ago
Roundtrip flight included
Detroit (DTW) 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
InterContinental Chicago Magnificent Mile by IHG
Downtown Chicago
per person
Aug 1 - Aug 4
found 19 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.
The location of the Intercontinental Magnificent Mile, Chicago cannot be better. It’s literally right smack dab in the middle of everything. We had an amazing weekend there. The room was comfortable and clean. The staff was friendly and we didn’t wait for anything we needed. Highly recommend, 10/10. Oh the pool is worth just asking a walk through. Super cool.
Reviewed on Jul 21, 2025
3 night Illinois 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
Oct 2 - Oct 5
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 Art Institute of Chicago are located nearby.
We came to town for a wedding and loved the location of the Palmer House. We spent much of the day before the event walking the city and sightseeing. It is a beautiful hotel.
Reviewed on Jul 28, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 2 - Oct 5
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, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The best hotel in Chicago!
Reviewed on Jul 4, 2025
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Orlando (MCO) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The room was spacious with a wonderful view and at a great price. The staff was helpful and responsive. The hotel is close to many Chicago attractions. Would definitely stay there again.
Reviewed on Jul 18, 2025
4 night Illinois Adventure vacation packages with flight
Price found within the past 48 hours. Click for updated prices.
The Buckingham Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Stay at this 3.5-star boutique hotel in Chicago. Enjoy parking (surcharge), a 24-hour front desk, and a 24-hour business center. Our guests praise the helpful staff in our reviews. Popular attractions Art Institute of Chicago and Grant Park are located nearby.
High-end rooms and great location in the south loop.
Reviewed on Jun 29, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Aug 1 - Aug 5
found 1 day ago
Roundtrip flight included
Dayton (DAY) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!
Reviewed on Jun 15, 2025
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip non-stop flight included
Gulfport (GPT) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The room was spacious with a wonderful view and at a great price. The staff was helpful and responsive. The hotel is close to many Chicago attractions. Would definitely stay there again.
Reviewed on Jul 18, 2025
5 night Illinois Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Wilkes-Barre (AVP) 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
Omni Chicago Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Huntington (HTS) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The room was spacious with a wonderful view and at a great price. The staff was helpful and responsive. The hotel is close to many Chicago attractions. Would definitely stay there again.
Reviewed on Jul 18, 2025
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Oct 2 - Oct 7
found 1 day ago
Roundtrip non-stop flight included
Wilkes-Barre (AVP) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!
Reviewed on Jun 15, 2025
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
per person
Sep 1 - Sep 7
found 3 hours ago
Roundtrip flight included
Miami (MIA) to Chicago (ORD)
Stay at this 4.5-star luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Unbelievable property, great hospitality, clean, beautiful rooms, lots of amenities, and of course there is the rooftop. I like that they allow guests to have priority on the rooftop in terms of going up there. We will be back for sure. Thank you, London house.!
Reviewed on Jun 15, 2025
Chicago Athletic Association, a Hyatt Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 12 - Oct 19
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, 2 restaurants, and 3 bars/lounges. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The best hotel in Chicago!
Reviewed on Jul 4, 2025
Kinzie Hotel
Downtown Chicago
Save 100% on your flight
per person
Oct 4 - Oct 11
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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
Adventure hotels in Illinois
Palmer House a Hilton Hotel
17 E Monroe St, Chicago, IL
Free Cancellation
Reserve now, pay when you stay
$198 nightly
The price is $229 total per night
$229 total
Aug 21 - Aug 22
Total includes taxes and fees
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, concierge services, and dry cleaning/laundry. 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
$209 nightly
The price is $245 total per night
$245 total
Aug 20 - Aug 21
Total includes taxes and fees
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 dry cleaning/laundry, concierge services, and securing valuables. 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
$241 nightly
The price is $283 total per night
$283 total
Aug 21 - Aug 22
Total includes taxes and fees
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 dry cleaning/laundry, securing valuables, and tours or tickets. 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 Illinois?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
LGA
LaGuardia
ORD
O'Hare Intl.
$90 Roundtrip, just found
$90
Roundtrip
just found
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$108 Roundtrip, just found
$108
Roundtrip
just found
LGA
LaGuardia
MDW
Midway Intl.
$117 Roundtrip, found 5 days ago
$117
Roundtrip
found 5 days ago
LGA
LaGuardia
STL
Lambert-St. Louis Intl.
$131 Roundtrip, found 3 days ago
$131
Roundtrip
found 3 days ago
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$160 Roundtrip, found 6 days ago
$160
Roundtrip
found 6 days ago
LGA
LaGuardia
RFD
Greater Rockford
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
LAX
Los Angeles Intl.
MDW
Midway Intl.
$197 Roundtrip, found 1 day ago
$197
Roundtrip
found 1 day ago
Hotel themes
- Hotels with Air Conditioning in Illinois
- Hotels with WiFi in Illinois
- Hotels with Restaurants in Illinois
- Kid Friendly Hotels in Illinois
- Hotels with Free Parking in Illinois
- Business Hotels in Illinois
- Hotels with Shopping in Illinois
- Hotels with Free Breakfast in Illinois
- Hotels with a Gym in Illinois
- Hotels with Pool in Illinois