Illinois Adventure Vacation Packages

Best Illinois Adventure packages

Price found within the past 48 hours. Click for updated prices.
Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Price was $994, price is now $727 per person
$727
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Good location

Reviewed on Sep 6, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,151, price is now $781 per person
$781
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop 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.

Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,735, price is now $1,272 per person
$1,272
per person
Oct 15 - Oct 18
found 1 day ago
Roundtrip flight included
Charlotte (CLT) 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.
Everyone was accommodating, responsive and friendly.

Reviewed on Sep 8, 2026

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 $985, price is now $677 per person
$677
per person
Nov 19 - Nov 22
found 11 hours ago
Roundtrip flight included
Charlotte (CLT) 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.

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,330, price is now $842 per person
$842
per person
Nov 14 - Nov 17
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.

Chicago Marriott Downtown Magnificent Mile

Chicago Marriott Downtown Magnificent Mile

4 out of 5
Downtown Chicago
Price was $994, price is now $727 per person
$727
per person
Oct 14 - Oct 17
found 1 day ago
Roundtrip non-stop flight included
Albuquerque (ABQ) to Chicago (ORD)
Book a stay at this business-friendly hotel in Chicago. Enjoy 2 restaurants, a rooftop terrace, and breakfast (surcharge). Our guests praise the bar and the helpful staff in our reviews. Popular attractions Michigan Avenue and Chicago Riverwalk are located nearby.
Good location

Reviewed on Sep 6, 2026

4 night Illinois Adventure vacation packages with flight

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
Save 100% on your flight
Price was $1,450, price is now $1,035 per person
$1,035
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) 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 staff was very helpful. The room was small but it was nice. It is busy in the city so noise can be an issue at night

Reviewed on Sep 10, 2026

Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
Downtown Chicago
Save 100% on your flight
Price was $1,728, price is now $1,112 per person
$1,112
per person
Oct 14 - Oct 18
found 1 day ago
Roundtrip flight included
Boston (BOS) 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.

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 $1,540, price is now $1,099 per person
$1,099
per person
Sep 17 - Sep 21
found 1 day ago
Roundtrip flight included
Denver (DEN) 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.

5 night Illinois Adventure vacation packages with airfare included

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 $2,114, price is now $1,429 per person
$1,429
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 $5,091, price is now $3,526 per person
$3,526
per person
Sep 16 - Sep 21
found 1 day ago
Roundtrip flight included
President Donald J. Trump Intl. Airport (DJT) 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.
Everyone was accommodating, responsive and friendly.

Reviewed on Sep 8, 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 $2,163, price is now $1,518 per person
$1,518
per person
Oct 14 - Oct 19
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) 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 staff was very helpful. The room was small but it was nice. It is busy in the city so noise can be an issue at night

Reviewed on Sep 10, 2026

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 $2,570, price is now $1,511 per person
$1,511
per person
Sep 24 - Sep 30
found 1 day ago
Roundtrip non-stop flight included
New York (NYC) 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
Price was $5,714, price is now $3,188 per person
$3,188
per person
Sep 17 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.
Everyone was accommodating, responsive and friendly.

Reviewed on Sep 8, 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 $3,225, price is now $2,182 per person
$2,182
per person
Oct 14 - Oct 21
found 1 hour ago
Roundtrip flight included
San Diego (SAN) 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 staff was very helpful. The room was small but it was nice. It is busy in the city so noise can be an issue at night

Reviewed on Sep 10, 2026

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
$306 nightly
The price is $364 total per night
$364 total
Sep 11 - Sep 12
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 luggage storage, concierge services, and access to locker space. 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
$294 nightly
The price is $349 total per night
$349 total
Sep 11 - Sep 12
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 concierge services, luggage storage, and securing valuables. 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
$324 nightly
The price is $385 total per night
$385 total
Sep 26 - Sep 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 dry cleaning/laundry, securing valuables, 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.

Thu, Oct 1 - Sat, Oct 3
DFW
Dallas-Fort Worth Intl.
ORD
O'Hare Intl.
$65 Roundtrip, found 1 hour ago
$65
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Thu, Oct 1 from Dallas-Fort Worth Intl. to O'Hare Intl., returning Sat, Oct 3, priced at $65 found 1 hour ago
Wed, Oct 21 - Sat, Oct 24
DFW
Dallas-Fort Worth Intl.
MDW
Midway Intl.
$67 Roundtrip, found 1 hour ago
$67
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Wed, Oct 21 from Dallas-Fort Worth Intl. to Midway Intl., returning Sat, Oct 24, priced at $67 found 1 hour ago
Fri, Oct 9 - Mon, Oct 12
DFW
Dallas-Fort Worth Intl.
STL
Lambert-St. Louis Intl.
$75 Roundtrip, found 10 hours ago
$75
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Fri, Oct 9 from Dallas-Fort Worth Intl. to Lambert-St. Louis Intl., returning Mon, Oct 12, priced at $75 found 10 hours ago
Sat, Oct 10 - Sat, Oct 17
LAX
Los Angeles Intl.
ORD
O'Hare Intl.
$100 Roundtrip, found 1 hour ago
$100
Roundtrip
found 1 hour ago
Select Frontier Airlines flight, departing Sat, Oct 10 from Los Angeles Intl. to O'Hare Intl., returning Sat, Oct 17, priced at $100 found 1 hour ago
Sat, Nov 14 - Mon, Nov 16
LAX
Los Angeles Intl.
STL
Lambert-St. Louis Intl.
$164 Roundtrip, found 7 hours ago
$164
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Nov 14 from Los Angeles Intl. to Lambert-St. Louis Intl., returning Mon, Nov 16, priced at $164 found 7 hours ago
Sat, Nov 7 - Wed, Nov 11
SEA
Seattle - Tacoma Intl.
ORD
O'Hare Intl.
$178 Roundtrip, found 10 hours ago
$178
Roundtrip
found 10 hours ago
Select Frontier Airlines flight, departing Sat, Nov 7 from Seattle - Tacoma Intl. to O'Hare Intl., returning Wed, Nov 11, priced at $178 found 10 hours ago
Fri, Nov 6 - Sun, Nov 8
SEA
Seattle - Tacoma Intl.
MDW
Midway Intl.
$197 Roundtrip, found 3 days ago
$197
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Fri, Nov 6 from Seattle - Tacoma Intl. to Midway Intl., returning Sun, Nov 8, priced at $197 found 3 days ago
Thu, Oct 1 - Mon, Oct 5
SEA
Seattle - Tacoma Intl.
STL
Lambert-St. Louis Intl.
$201 Roundtrip, found 12 hours ago
$201
Roundtrip
found 12 hours ago
Select Frontier Airlines flight, departing Thu, Oct 1 from Seattle - Tacoma Intl. to Lambert-St. Louis Intl., returning Mon, Oct 5, priced at $201 found 12 hours ago
Fri, Oct 23 - Mon, Oct 26
LAX
Los Angeles Intl.
MDW
Midway Intl.
$217 Roundtrip, found 11 hours ago
$217
Roundtrip
found 11 hours ago
Select Southwest Airlines flight, departing Fri, Oct 23 from Los Angeles Intl. to Midway Intl., returning Mon, Oct 26, priced at $217 found 11 hours ago
Wed, Sep 30 - Wed, Oct 7
LGA
LaGuardia
STL
Lambert-St. Louis Intl.
$220 Roundtrip, found 8 hours ago
$220
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Wed, Sep 30 from LaGuardia to Lambert-St. Louis Intl., returning Wed, Oct 7, priced at $220 found 8 hours ago
Tue, Sep 29 - Wed, Sep 30
LGA
LaGuardia
ORD
O'Hare Intl.
$222 Roundtrip, found 8 hours ago
$222
Roundtrip
found 8 hours ago
Select Frontier Airlines flight, departing Tue, Sep 29 from LaGuardia to O'Hare Intl., returning Wed, Sep 30, priced at $222 found 8 hours ago
Wed, Sep 30 - Wed, Oct 7
LGA
LaGuardia
MDW
Midway Intl.
$232 Roundtrip, found 4 hours ago
$232
Roundtrip
found 4 hours ago
Select Frontier Airlines flight, departing Wed, Sep 30 from LaGuardia to Midway Intl., returning Wed, Oct 7, priced at $232 found 4 hours ago
Mon, Nov 16 - Thu, Nov 19
DAL
Love Field
STL
Lambert-St. Louis Intl.
$237 Roundtrip, found 6 days ago
$237
Roundtrip
found 6 days ago
Select Southwest Airlines flight, departing Mon, Nov 16 from Love Field to Lambert-St. Louis Intl., returning Thu, Nov 19, priced at $237 found 6 days ago
Sun, Sep 27 - Wed, Sep 30
LAX
Los Angeles Intl.
RFD
Greater Rockford
$257 Roundtrip, found 4 days ago
$257
Roundtrip
found 4 days ago
Select American Airlines flight, departing Sun, Sep 27 from Los Angeles Intl. to Greater Rockford, returning Wed, Sep 30, priced at $257 found 4 days ago

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