Illinois Adventure Vacation Packages

Best Illinois Adventure packages

Price found within the past 48 hours. Click for updated prices.
The Westin Chicago River North

The Westin Chicago River North

4.5 out of 5
Downtown Chicago
Price was $477, price is now $368 per person
$368
per person
Jan 1 - Jan 4
found 20 hours ago
Roundtrip flight included
Baltimore (BWI) to Chicago (ORD)
Book a stay at this 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 fiancé loved it. We had a great time. She actually wants to move there.

Reviewed on Sep 15, 2025

The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
Price was $513, price is now $389 per person
$389
per person
Jan 3 - Jan 7
found 23 hours ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
Book a stay at this 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 Millennium Park and Chicago Riverwalk are located nearby.
High-end rooms and great location in the south loop.

Reviewed on Jun 29, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Price was $556, price is now $443 per person
$443
per person
Jan 1 - Jan 4
found 1 day ago
Roundtrip flight included
Nashville (BNA) 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.
Pendry was historic and great

Reviewed on Jul 5, 2024

3 night Illinois Adventure vacation packages with airfare

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $363, price is now $213 per person
$213
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this luxury 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.
I loved the architecture and the history of the hotel.

Reviewed on Oct 20, 2025

Sofitel Chicago Magnificent Mile

Sofitel Chicago Magnificent Mile

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $405, price is now $283 per person
$283
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Book a stay at this luxury 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.
Hotel was amazing. Surrounding area was good too.

Reviewed on Oct 1, 2025

The Buckingham Hotel

The Buckingham Hotel

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $410, price is now $304 per person
$304
per person
Feb 5 - Feb 8
found 1 day ago
Roundtrip flight included
New York (NYC) to Chicago (ORD)
Book a stay at this 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 Millennium Park and Chicago Riverwalk are located nearby.
High-end rooms and great location in the south loop.

Reviewed on Jun 29, 2025

4 night Illinois Adventure vacation packages with flight

Price found within the past 48 hours. Click for updated prices.
Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $608, price is now $371 per person
$371
per person
Feb 3 - Feb 7
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.
Pendry was historic and great

Reviewed on Jul 5, 2024

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Price was $548, price is now $384 per person
$384
per person
Dec 4 - Dec 8
found 5 hours ago
Roundtrip flight included
Fort Lauderdale (FLL) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Chicago Riverwalk are located nearby.
The staff were amazing , very friendly and made us feel at home.

Reviewed on Oct 23, 2025

Hilton Chicago

Hilton Chicago

4 out of 5
Downtown Chicago
Price was $593, price is now $418 per person
$418
per person
Feb 2 - Feb 6
found 1 day ago
Roundtrip flight included
San Diego (SAN) to Chicago (ORD)
Book a stay at this historic hotel in Chicago. Enjoy 2 restaurants, breakfast (surcharge), and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Millennium Park and Soldier Field are located nearby.
Nice, clean hotel, friendly staff, very comfortable room, within walking distance from lake Michigan, major attractions, shopping and dining.

Reviewed on Sep 5, 2025

5 night Illinois Adventure vacation packages with airfare included

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $604, price is now $370 per person
$370
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip flight included
Austin (AUS) to Chicago (ORD)
Book a stay at this luxury 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.
I loved the architecture and the history of the hotel.

Reviewed on Oct 20, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $684, price is now $392 per person
$392
per person
Feb 8 - Feb 13
found 1 day ago
Roundtrip flight included
Austin (AUS) 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.
Pendry was historic and great

Reviewed on Jul 5, 2024

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $980, price is now $589 per person
$589
per person
Dec 11 - Dec 16
found 1 day ago
Roundtrip flight included
Nashville (BNA) to Chicago (ORD)
Book a stay at this 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.
Rooms small but clean.

Reviewed on Aug 14, 2025

Adventure vacation packages for 6-7 nights

Price found within the past 48 hours. Click for updated prices.
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
Downtown Chicago
Price was $906, price is now $538 per person
$538
per person
Feb 4 - Feb 11
just found
Roundtrip non-stop flight included
San Juan (SJU) to Chicago (ORD)
Book a stay at this luxury 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.
I loved the architecture and the history of the hotel.

Reviewed on Oct 20, 2025

Pendry Chicago

Pendry Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $985, price is now $574 per person
$574
per person
Feb 3 - Feb 10
found 19 hours ago
Roundtrip flight included
San Juan (SJU) 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.
Pendry was historic and great

Reviewed on Jul 5, 2024

Chicago Athletic Association, a Hyatt Hotel

Chicago Athletic Association, a Hyatt Hotel

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,022, price is now $613 per person
$613
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this 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.
Rooms small but clean.

Reviewed on Aug 14, 2025

Adventure hotels in Illinois

Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

4 out of 5
17 E Monroe St Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $153 total per night
$153 total
per night
Dec 28 - Dec 29
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 securing valuables, access to locker space, 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

Hyatt Regency McCormick Place Chicago

4 out of 5
2233 S Martin Luther King Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $257 total per night
$257 total
per night
Dec 4 - Dec 5
At Hyatt Regency McCormick Place Chicago , guests have access to a gym, a sauna, and free WiFi in public areas. 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 luggage storage, concierge services, and dry cleaning/laundry. Additional amenities include meeting rooms, a conference center, and a 24-hour business center.
Free WiFi
Restaurant
Hyatt Regency Chicago

Hyatt Regency Chicago

4 out of 5
151 East Wacker Dr Chicago IL
Free Cancellation
Reserve now, pay when you stay
The price is $189 total per night
$189 total
per night
Dec 22 - Dec 23
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 securing valuables, luggage storage, and concierge services. Additional amenities include conference space, a business center, and express check-in.
Free WiFi
Restaurant
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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.

Fri, Feb 20 - Sun, Mar 1
MCO
Orlando Intl.
MDW
Midway Intl.
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Feb 20 from Orlando Intl. to Midway Intl., returning Sun, Mar 1, priced at $58 just found
Thu, Jan 22 - Wed, Jan 28
MCO
Orlando Intl.
STL
Lambert-St. Louis Intl.
$59 Roundtrip, found 3 hours ago
$59
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Jan 22 from Orlando Intl. to Lambert-St. Louis Intl., returning Wed, Jan 28, priced at $59 found 3 hours ago
Fri, Feb 13 - Sun, Feb 15
IAH
George Bush Intercontinental
MDW
Midway Intl.
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Feb 13 from George Bush Intercontinental to Midway Intl., returning Sun, Feb 15, priced at $68 found 1 hour ago
Fri, Feb 13 - Sun, Feb 15
IAH
George Bush Intercontinental
ORD
O'Hare Intl.
$68 Roundtrip, found 1 hour ago
$68
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Fri, Feb 13 from George Bush Intercontinental to O'Hare Intl., returning Sun, Feb 15, priced at $68 found 1 hour ago
Thu, Feb 19 - Mon, Feb 23
MCO
Orlando Intl.
ORD
O'Hare Intl.
$73 Roundtrip, found 3 hours ago
$73
Roundtrip
found 3 hours ago
Select Frontier Airlines flight, departing Thu, Feb 19 from Orlando Intl. to O'Hare Intl., returning Mon, Feb 23, priced at $73 found 3 hours ago
Sun, Jan 18 - Mon, Jan 26
AUS
Austin-Bergstrom Intl.
ORD
O'Hare Intl.
$83 Roundtrip, found 2 days ago
$83
Roundtrip
found 2 days ago
Select Frontier Airlines flight, departing Sun, Jan 18 from Austin-Bergstrom Intl. to O'Hare Intl., returning Mon, Jan 26, priced at $83 found 2 days ago
Fri, Jan 23 - Fri, Jan 30
MCO
Orlando Intl.
EVV
Evansville Regional
$102 Roundtrip, just found
$102
Roundtrip
just found
Select Breeze Airways flight, departing Fri, Jan 23 from Orlando Intl. to Evansville Regional, returning Fri, Jan 30, priced at $102 just found
Sat, Jan 10 - Sat, Jan 17
MCO
Orlando Intl.
SPI
Abraham Lincoln Capital
$122 Roundtrip, found 7 hours ago
$122
Roundtrip
found 7 hours ago
Select Breeze Airways flight, departing Sat, Jan 10 from Orlando Intl. to Abraham Lincoln Capital, returning Sat, Jan 17, priced at $122 found 7 hours ago
Sun, Dec 7 - Thu, Dec 11
AUS
Austin-Bergstrom Intl.
STL
Lambert-St. Louis Intl.
$130 Roundtrip, found 5 days ago
$130
Roundtrip
found 5 days ago
Select Spirit Airlines flight, departing Sun, Dec 7 from Austin-Bergstrom Intl. to Lambert-St. Louis Intl., returning Thu, Dec 11, priced at $130 found 5 days ago
Thu, Jan 15 - Sun, Jan 18
AUS
Austin-Bergstrom Intl.
MDW
Midway Intl.
$170 Roundtrip, found 5 days ago
$170
Roundtrip
found 5 days ago
Select Southwest Airlines flight, departing Thu, Jan 15 from Austin-Bergstrom Intl. to Midway Intl., returning Sun, Jan 18, priced at $170 found 5 days ago
Thu, Jan 15 - Sat, Jan 17
AUS
Austin-Bergstrom Intl.
RFD
Greater Rockford
$171 Roundtrip, found 6 days ago
$171
Roundtrip
found 6 days ago
Select American Airlines flight, departing Thu, Jan 15 from Austin-Bergstrom Intl. to Greater Rockford, returning Sat, Jan 17, priced at $171 found 6 days ago
Fri, Jan 30 - Sun, Feb 1
DRO
La Plata County
STL
Lambert-St. Louis Intl.
$200 Roundtrip, found 5 days ago
$200
Roundtrip
found 5 days ago
Select American Airlines flight, departing Fri, Jan 30 from La Plata County to Lambert-St. Louis Intl., returning Sun, Feb 1, priced at $200 found 5 days ago
Fri, Dec 12 - Sun, Dec 14
DRO
La Plata County
PIA
Greater Peoria Regional
$233 Roundtrip, found 5 hours ago
$233
Roundtrip
found 5 hours ago
Select American Airlines flight, departing Fri, Dec 12 from La Plata County to Greater Peoria Regional, returning Sun, Dec 14, priced at $233 found 5 hours ago
Thu, Mar 26 - Mon, Mar 30
DRO
La Plata County
ORD
O'Hare Intl.
$235 Roundtrip, found 5 days ago
$235
Roundtrip
found 5 days ago
Select United flight, departing Thu, Mar 26 from La Plata County to O'Hare Intl., returning Mon, Mar 30, priced at $235 found 5 days ago

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