Illinois Adventure Vacation Packages

Best Illinois Adventure packages

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 $1,000, price is now $670 per person
$670
per person
Sep 10 - Sep 13
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 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.
Beautiful hotel and great staff. I also ate at the restaurant in the building, venteux and that was really good too. I would stay here again! It’s within walking distance of a lot of restaurants and sights (definitely do the riverwalk and the architecture boat tour). I could hear all the traffic from the street, but that’s to be expected when being in the middle of a large city. I had a fun time in Chicago!

Reviewed on Aug 7, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,899, price is now $1,557 per person
$1,557
per person
Aug 10 - Aug 13
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 full-service spa, and breakfast (surcharge). Our guests praise 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 $1,024, price is now $676 per person
$676
per person
Sep 10 - Sep 13
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.

3 night Illinois Adventure vacation packages with airfare

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 $1,000, price is now $670 per person
$670
per person
Sep 10 - Sep 13
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 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.
Beautiful hotel and great staff. I also ate at the restaurant in the building, venteux and that was really good too. I would stay here again! It’s within walking distance of a lot of restaurants and sights (definitely do the riverwalk and the architecture boat tour). I could hear all the traffic from the street, but that’s to be expected when being in the middle of a large city. I had a fun time in Chicago!

Reviewed on Aug 7, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $2,899, price is now $1,557 per person
$1,557
per person
Aug 10 - Aug 13
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 full-service spa, and breakfast (surcharge). Our guests praise 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 $1,136, price is now $710 per person
$710
per person
Oct 13 - Oct 16
found 1 hour ago
Roundtrip flight included
Baltimore (BWI) 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.

4 night Illinois Adventure vacation packages with flight

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 $1,348, price is now $920 per person
$920
per person
Oct 13 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Palm Springs (PSP) 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.

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $4,575, price is now $3,031 per person
$3,031
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Boise (BOI) to Chicago (ORD)
Book a stay at this luxury hotel in Chicago. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

4.5 out of 5
Downtown Chicago
Price was $1,380, price is now $1,029 per person
$1,029
per person
Sep 10 - Sep 14
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) 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.
The Whitehall Hotel, BW Premier Collection

The Whitehall Hotel, BW Premier Collection

3.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,171, price is now $780 per person
$780
per person
Oct 11 - Oct 16
found 4 hours ago
Roundtrip flight included
Los Angeles (LAX) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The breakfast was very minimal.

Reviewed on Aug 7, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,605, price is now $918 per person
$918
per person
Aug 11 - Aug 16
found 23 hours 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.

Silversmith Hotel Chicago Downtown

Silversmith Hotel Chicago Downtown

4 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,813, price is now $1,200 per person
$1,200
per person
Oct 11 - Oct 16
found 4 hours 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 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.

Adventure vacation packages for 6-7 nights

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
Save 100% on your flight
Price was $1,540, price is now $1,030 per person
$1,030
per person
Sep 10 - Sep 16
found 1 day ago
Roundtrip flight included
Indianapolis (IND) to Chicago (ORD)
Book a stay at this boutique hotel in Chicago. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
The breakfast was very minimal.

Reviewed on Aug 7, 2026

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Price was $4,740, price is now $2,744 per person
$2,744
per person
Sep 13 - Sep 19
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 breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.

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 $2,087, price is now $1,386 per person
$1,386
per person
Sep 10 - Sep 16
found 1 day ago
Roundtrip flight included
Indianapolis (IND) 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 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
$199 nightly
The price is $237 total per night
$237 total
Sep 7 - Sep 8
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.
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
$211 nightly
The price is $251 total per night
$251 total
Sep 1 - Sep 2
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 tours or tickets, dry cleaning/laundry, and luggage storage. 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
$254 nightly
The price is $302 total per night
$302 total
Aug 30 - Aug 31
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 concierge services, dry cleaning/laundry, and luggage storage. 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.

Thu, Oct 8 - Mon, Oct 12
ATL
Hartsfield-Jackson Atlanta Intl.
STL
Lambert-St. Louis Intl.
$46 Roundtrip, just found
$46
Roundtrip
just found
Select Frontier Airlines flight, departing Thu, Oct 8 from Hartsfield-Jackson Atlanta Intl. to Lambert-St. Louis Intl., returning Mon, Oct 12, priced at $46 just found
Fri, Aug 28 - Tue, Sep 1
ATL
Hartsfield-Jackson Atlanta Intl.
ORD
O'Hare Intl.
$120 Roundtrip, just found
$120
Roundtrip
just found
Select Frontier Airlines flight, departing Fri, Aug 28 from Hartsfield-Jackson Atlanta Intl. to O'Hare Intl., returning Tue, Sep 1, priced at $120 just found
Wed, Aug 12 - Sun, Aug 16
ATL
Hartsfield-Jackson Atlanta Intl.
MDW
Midway Intl.
$160 Roundtrip, found 4 hours ago
$160
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Aug 12 from Hartsfield-Jackson Atlanta Intl. to Midway Intl., returning Sun, Aug 16, priced at $160 found 4 hours ago
Wed, Sep 2 - Tue, Sep 8
EWR
Newark Liberty Intl. Airport
MDW
Midway Intl.
$168 Roundtrip, just found
$168
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Sep 2 from Newark Liberty Intl. Airport to Midway Intl., returning Tue, Sep 8, priced at $168 just found
Wed, Sep 9 - Tue, Sep 15
EWR
Newark Liberty Intl. Airport
ORD
O'Hare Intl.
$168 Roundtrip, just found
$168
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Sep 9 from Newark Liberty Intl. Airport to O'Hare Intl., returning Tue, Sep 15, priced at $168 just found
Sat, Aug 29 - Sat, Sep 5
EWR
Newark Liberty Intl. Airport
RFD
Greater Rockford
$209 Roundtrip, found 6 days ago
$209
Roundtrip
found 6 days ago
Select American Airlines flight, departing Sat, Aug 29 from Newark Liberty Intl. Airport to Greater Rockford, returning Sat, Sep 5, priced at $209 found 6 days ago
Tue, Sep 1 - Wed, Sep 2
JFK
John F. Kennedy Intl.
ORD
O'Hare Intl.
$227 Roundtrip, just found
$227
Roundtrip
just found
Select Delta flight, departing Tue, Sep 1 from John F. Kennedy Intl. to O'Hare Intl., returning Wed, Sep 2, priced at $227 just found
Fri, Aug 28 - Mon, Oct 26
EWR
Newark Liberty Intl. Airport
STL
Lambert-St. Louis Intl.
$232 Roundtrip, found 21 hours ago
$232
Roundtrip
found 21 hours ago
Select Frontier Airlines flight, departing Fri, Aug 28 from Newark Liberty Intl. Airport to Lambert-St. Louis Intl., returning Mon, Oct 26, priced at $232 found 21 hours ago
Sat, Sep 26 - Tue, Sep 29
JFK
John F. Kennedy Intl.
RFD
Greater Rockford
$239 Roundtrip, found 2 days ago
$239
Roundtrip
found 2 days ago
Select American Airlines flight, departing Sat, Sep 26 from John F. Kennedy Intl. to Greater Rockford, returning Tue, Sep 29, priced at $239 found 2 days ago
Thu, Sep 10 - Fri, Sep 11
ATL
Hartsfield-Jackson Atlanta Intl.
RFD
Greater Rockford
$241 Roundtrip, found 22 hours ago
$241
Roundtrip
found 22 hours ago
Select American Airlines flight, departing Thu, Sep 10 from Hartsfield-Jackson Atlanta Intl. to Greater Rockford, returning Fri, Sep 11, priced at $241 found 22 hours ago
Fri, Sep 11 - Sun, Sep 13
ATL
Hartsfield-Jackson Atlanta Intl.
EVV
Evansville Regional
$259 Roundtrip, found 1 hour ago
$259
Roundtrip
found 1 hour ago
Select Delta flight, departing Fri, Sep 11 from Hartsfield-Jackson Atlanta Intl. to Evansville Regional, returning Sun, Sep 13, priced at $259 found 1 hour ago

More to Explore