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

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $847, price is now $698 per person
$698
per person
Nov 28 - Dec 1
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) 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.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,086, price is now $810 per person
$810
per person
Nov 28 - Dec 1
found 23 hours ago
Roundtrip flight included
Cleveland (CLE) 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.
Had a great stay, if you wear makeup be sure to pack a cloth and clenser for your face, but over all they did a wonderful job, be warned if you do over night valet it make take 20+ minutes to get your car back after 8pm, even if calling ahead of time to pick up your car

Reviewed on Oct 25, 2026

Hyatt Centric Chicago Magnificent Mile

Hyatt Centric Chicago Magnificent Mile

4 out of 5
Downtown Chicago
Price was $872, price is now $700 per person
$700
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.

3 night Illinois Adventure vacation packages with airfare

Price found within the past 48 hours. Click for updated prices.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Price was $384, price is now $291 per person
$291
per person
Dec 29 - Jan 1
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The staff here were great! Helped me with early check in and greeted me every single time I walked in. I’d stay again.

Reviewed on Oct 25, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $639, price is now $456 per person
$456
per person
Dec 29 - Jan 1
just found
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.
Had a great stay, if you wear makeup be sure to pack a cloth and clenser for your face, but over all they did a wonderful job, be warned if you do over night valet it make take 20+ minutes to get your car back after 8pm, even if calling ahead of time to pick up your car

Reviewed on Oct 25, 2026

Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $591, price is now $438 per person
$438
per person
Dec 29 - Jan 1
just found
Roundtrip flight included
Atlanta (ATL) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Friendly, helpful staff. Great accommodations and recommendations, with a central location and easy access to transportation.

Reviewed on Oct 25, 2026

4 night Illinois Adventure vacation packages with flight

Price found within the past 48 hours. Click for updated prices.
Kinzie Hotel

Kinzie Hotel

4 out of 5
Downtown Chicago
Price was $848, price is now $609 per person
$609
per person
Dec 29 - Jan 2
found 21 hours ago
Roundtrip flight included
Houston (IAH) to Chicago (ORD)
Book a stay at this spa hotel in Chicago. Enjoy a full-service spa, room service, and a fitness center. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Chicago Riverwalk and Michigan Avenue are located nearby.
Friendly, helpful staff. Great accommodations and recommendations, with a central location and easy access to transportation.

Reviewed on Oct 25, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Price was $1,071, price is now $733 per person
$733
per person
Dec 29 - Jan 2
found 18 hours ago
Roundtrip flight included
Nashville (BNA) 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.
Had a great stay, if you wear makeup be sure to pack a cloth and clenser for your face, but over all they did a wonderful job, be warned if you do over night valet it make take 20+ minutes to get your car back after 8pm, even if calling ahead of time to pick up your car

Reviewed on Oct 25, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,092, price is now $1,489 per person
$1,489
per person
Oct 28 - Nov 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.

5 night Illinois Adventure vacation packages with airfare included

Price found within the past 48 hours. Click for updated prices.
InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Price was $901, price is now $664 per person
$664
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Fort Myers (FMY) to Chicago (ORD)
Book a stay at this 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.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,055, price is now $683 per person
$683
per person
Dec 29 - Jan 3
found 1 day ago
Roundtrip flight included
Fort Myers (FMY) 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.
Had a great stay, if you wear makeup be sure to pack a cloth and clenser for your face, but over all they did a wonderful job, be warned if you do over night valet it make take 20+ minutes to get your car back after 8pm, even if calling ahead of time to pick up your car

Reviewed on Oct 25, 2026

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,304, price is now $947 per person
$947
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
Miami (MIA) 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.

Adventure vacation packages for 6-7 nights

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

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $998, price is now $549 per person
$549
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) 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.
Had a great stay, if you wear makeup be sure to pack a cloth and clenser for your face, but over all they did a wonderful job, be warned if you do over night valet it make take 20+ minutes to get your car back after 8pm, even if calling ahead of time to pick up your car

Reviewed on Oct 25, 2026

Sheraton Grand Chicago Riverwalk

Sheraton Grand Chicago Riverwalk

4 out of 5
Downtown Chicago
Price was $2,135, price is now $988 per person
$988
per person
Nov 22 - Nov 28
found 19 hours ago
Roundtrip flight included
Denver (DEN) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 3 restaurants, 2 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

InterContinental Chicago Magnificent Mile by IHG

InterContinental Chicago Magnificent Mile by IHG

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $853, price is now $565 per person
$565
per person
Dec 29 - Jan 4
found 1 day ago
Roundtrip flight included
Minneapolis (MSP) to Chicago (ORD)
Book a stay at this 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.

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
$153 nightly
The price is $181 total per night
$181 total
Nov 24 - Nov 25
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 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
$224 nightly
The price is $266 total per night
$266 total
Nov 23 - Nov 24
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 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
$205 nightly
The price is $244 total per night
$244 total
Nov 23 - Nov 24
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 securing valuables, luggage storage, and concierge services. Additional amenities include conference space, a business center, and express check-in.
Free WiFi
Restaurant
Don't see what you're looking for?
See all available properties in Illinois
View all properties
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.

Sat, Nov 14 - Wed, Nov 18
DEN
Denver Intl.
ORD
O'Hare Intl.
$58 Roundtrip, just found
$58
Roundtrip
just found
Select Frontier Airlines flight, departing Sat, Nov 14 from Denver Intl. to O'Hare Intl., returning Wed, Nov 18, priced at $58 just found
Fri, Nov 13 - Sat, Nov 14
DEN
Denver Intl.
STL
Lambert-St. Louis Intl.
$74 Roundtrip, found 5 days ago
$74
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Fri, Nov 13 from Denver Intl. to Lambert-St. Louis Intl., returning Sat, Nov 14, priced at $74 found 5 days ago
Wed, Dec 2 - Sat, Dec 5
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$76 Roundtrip, found 21 hours ago
$76
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Wed, Dec 2 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Dec 5, priced at $76 found 21 hours ago
Tue, Dec 8 - Wed, Dec 9
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$76 Roundtrip, found 15 hours ago
$76
Roundtrip
found 15 hours ago
Select Frontier Airlines flight, departing Tue, Dec 8 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Wed, Dec 9, priced at $76 found 15 hours ago
Thu, Nov 12 - Mon, Nov 16
DFW
Dallas-Fort Worth Intl.
STL
Lambert-St. Louis Intl.
$98 Roundtrip, found 8 hours ago
$98
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Dallas-Fort Worth Intl. to Lambert-St. Louis Intl., returning Mon, Nov 16, priced at $98 found 8 hours ago
Wed, Feb 17 - Sat, Feb 20
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$119 Roundtrip, found 14 hours ago
$119
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Wed, Feb 17 from Los Angeles Intl. to O'Hare Intl., returning Sat, Feb 20, priced at $119 found 14 hours ago
Thu, Dec 3 - Mon, Dec 7
DEN
Denver Intl.
MDW
Midway Intl.
$142 Roundtrip, found 4 days ago
$142
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Dec 3 from Denver Intl. to Midway Intl., returning Mon, Dec 7, priced at $142 found 4 days ago
Fri, Dec 4 - Mon, Dec 7
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$155 Roundtrip, found 14 hours ago
$155
Roundtrip
found 14 hours ago
Select Frontier Airlines flight, departing Fri, Dec 4 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Mon, Dec 7, priced at $155 found 14 hours ago
Thu, Oct 29 - Thu, Oct 29
DEN
Denver Intl.
PIA
Greater Peoria Regional
$185 Roundtrip, found 6 days ago
$185
Roundtrip
found 6 days ago
Select Allegiant Air flight, departing Thu, Oct 29 from Denver Intl. to Greater Peoria Regional, returning Thu, Oct 29, priced at $185 found 6 days ago
Sat, Dec 5 - Wed, Dec 9
DAL
Love Field
MDW
Midway Intl.
$198 Roundtrip, found 1 day ago
$198
Roundtrip
found 1 day ago
Select Delta flight, departing Sat, Dec 5 from Love Field to Midway Intl., returning Wed, Dec 9, priced at $198 found 1 day ago
Thu, Nov 12 - Wed, Nov 18
LAX
Los Angeles Intl.
MDW
Midway Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Thu, Nov 12 from Los Angeles Intl. to Midway Intl., returning Wed, Nov 18, priced at $200 found 1 day ago
Thu, Dec 3 - Tue, Dec 8
DAL
Love Field
ORD
O'Hare Intl.
$209 Roundtrip, found 2 days ago
$209
Roundtrip
found 2 days ago
Select Delta flight, departing Thu, Dec 3 from Love Field to O'Hare Intl., returning Tue, Dec 8, priced at $209 found 2 days ago
Tue, Nov 10 - Thu, Nov 12
DAL
Love Field
STL
Lambert-St. Louis Intl.
$213 Roundtrip, found 1 day ago
$213
Roundtrip
found 1 day ago
Select Southwest Airlines flight, departing Tue, Nov 10 from Love Field to Lambert-St. Louis Intl., returning Thu, Nov 12, priced at $213 found 1 day ago
Thu, Dec 3 - Sun, Dec 6
DAL
Love Field
MLI
Quad City Intl.
$453 Roundtrip, found 1 day ago
$453
Roundtrip
found 1 day ago
Select Delta flight, departing Thu, Dec 3 from Love Field to Quad City Intl., returning Sun, Dec 6, priced at $453 found 1 day ago

More to Explore