Illinois Adventure Vacation Packages
Best Illinois Adventure packages
Price found within the past 48 hours. Click for updated prices.
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $734, price is now $493 per person
$493
per person
Jun 30 - Jul 3
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Price was $2,528, price is now $2,062 per person
$2,062
per person
May 28 - May 31
found 13 hours ago
Roundtrip flight included
Detroit (DTW) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The bell hoppers were all very pleasant each and every time we left and came back inside!
Reviewed on May 16, 2026
The Peninsula Chicago
Downtown Chicago
Price was $1,654, price is now $1,366 per person
$1,366
per person
Jun 28 - Jul 1
found 16 hours ago
Roundtrip flight included
Jacksonville (JAX) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Everything was superb. The only “complaint “ I have, is that I paid for a city view room, but actually looked at the side of one building. Other than that, we lived the stay.
Reviewed on Oct 24, 2025
3 night Illinois Adventure vacation packages with airfare
Price found within the past 48 hours. Click for updated prices.
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,205, price is now $865 per person
$865
per person
Jul 29 - Aug 1
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, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Room design, checking nd check out experience, general cleanliness etc
Reviewed on Feb 10, 2026
Swissotel - Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,484, price is now $907 per person
$907
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $1,538, price is now $1,090 per person
$1,090
per person
Jul 29 - Aug 1
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The bell hoppers were all very pleasant each and every time we left and came back inside!
Reviewed on May 16, 2026
4 night Illinois 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
Price was $1,061, price is now $671 per person
$671
per person
Jun 30 - Jul 4
found 14 hours ago
Roundtrip non-stop flight included
Columbia (CAE) to Chicago (ORD)
Book a stay at this luxury 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.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $3,132, price is now $2,243 per person
$2,243
per person
May 28 - Jun 1
found 15 hours ago
Roundtrip non-stop flight included
El Paso (ELP) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The bell hoppers were all very pleasant each and every time we left and came back inside!
Reviewed on May 16, 2026
The Peninsula Chicago
Downtown Chicago
Save 100% on your flight
Price was $2,191, price is now $1,611 per person
$1,611
per person
Jun 30 - Jul 4
found 17 hours ago
Roundtrip flight included
West Palm Beach (PBI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Everything was superb. The only “complaint “ I have, is that I paid for a city view room, but actually looked at the side of one building. Other than that, we lived the stay.
Reviewed on Oct 24, 2025
5 night Illinois Adventure vacation packages with airfare included
Price found within the past 48 hours. Click for updated prices.
Hyatt Centric Chicago Magnificent Mile
Downtown Chicago
Save 100% on your flight
Price was $1,828, price is now $1,254 per person
$1,254
per person
Jul 29 - Aug 3
found 16 hours ago
Roundtrip flight included
Boston (BOS) 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 helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Room design, checking nd check out experience, general cleanliness etc
Reviewed on Feb 10, 2026
Swissotel - Chicago
Downtown Chicago
Price was $2,505, price is now $1,478 per person
$1,478
per person
Jul 29 - Aug 3
found 1 day ago
Roundtrip flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this luxury 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.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $3,098, price is now $2,014 per person
$2,014
per person
May 28 - Jun 2
found 24 hours ago
Roundtrip flight included
Wilmington (ILM) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The bell hoppers were all very pleasant each and every time we left and came back inside!
Reviewed on May 16, 2026
Adventure vacation packages for 6-7 nights
Price found within the past 48 hours. Click for updated prices.
Pendry Chicago
Downtown Chicago
Save 100% on your flight
Price was $1,745, price is now $1,138 per person
$1,138
per person
Aug 9 - Aug 15
found 1 day ago
Roundtrip flight included
Columbus (CMH) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a rooftop terrace, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Millennium Park are located nearby.
Room was clean and comfortable. We really appreciated the chocolates and water!
Reviewed on Feb 25, 2026
Swissotel - Chicago
Downtown Chicago
Price was $2,626, price is now $1,364 per person
$1,364
per person
Jul 29 - Aug 4
found 1 day ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Book a stay at this luxury 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.
Great stay and we highly recommend. We will be back.
Reviewed on Apr 21, 2026
LondonHouse Chicago, Curio Collection by Hilton
Downtown Chicago
Save 100% on your flight
Price was $2,562, price is now $1,540 per person
$1,540
per person
Jul 29 - Aug 4
found 1 day ago
Roundtrip flight included
Houston (HOU) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
The bell hoppers were all very pleasant each and every time we left and came back inside!
Reviewed on May 16, 2026
Adventure hotels in Illinois
Palmer House a Hilton Hotel
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
$237 nightly
The price is $282 total per night
$282 total
May 26 - May 27
Total with 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, securing valuables, and luggage storage. Other amenities at this luxury 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
$314 nightly
The price is $373 total per night
$373 total
May 27 - May 28
Total with taxes and fees
At Hyatt Regency McCormick Place Chicago , guests have access to a gym, a sauna, and free WiFi in public areas. Valet parking is offered for USD 60 per day. Multilingual staff at the 24-hour front desk can assist with securing valuables, dry cleaning/laundry, and tours or tickets. Additional amenities include meeting rooms, a conference center, and a 24-hour business center.
Free WiFi
Restaurant
Hyatt Regency Chicago
151 East Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
$264 nightly
The price is $314 total per night
$314 total
May 26 - May 27
Total with 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 92 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 Illinois?
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$172 Roundtrip, found 13 hours ago
$172
Roundtrip
found 13 hours ago
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$176 Roundtrip, found 5 days ago
$176
Roundtrip
found 5 days ago
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$177 Roundtrip, just found
$177
Roundtrip
just found
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$197 Roundtrip, found 2 days ago
$197
Roundtrip
found 2 days ago
JFK
John F. Kennedy Intl.
RFD
Greater Rockford
$206 Roundtrip, found 2 days ago
$206
Roundtrip
found 2 days ago
EWR
Newark Liberty Intl. Airport
STL
Lambert-St. Louis Intl.
$209 Roundtrip, found 6 days ago
$209
Roundtrip
found 6 days ago
EWR
Newark Liberty Intl. Airport
MLI
Quad City Intl.
$281 Roundtrip, found 18 hours ago
$281
Roundtrip
found 18 hours ago
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