Hike & Dine Events presents The Fall Finale Trip: Illinois Edition

Oct 24, 2026 to Oct 26, 2026
Illinois

Our Last Trip of the Year | October 24–26, 2026

THIS IS THE FINALE

We’re closing out our 2026 hiking season with one last getaway, and we’re taking it to Illinois.

Picture crisp fall air, colorful trails, breathtaking views, good food, a night out in full costume, and a Chicago weekend with plenty to explore. We’ll hike through Starved Rock and Matthiessen State Parks, experience one of the largest fall festival in the Midwest, and leave plenty of room for everyone to enjoy Chicago their own way.

Before booking: This trip requires an active Travel Membership. You may book using either the Single-Trip Travel Membership or Annual Travel Membership. Your trip booking must be completed under one of these memberships.

THE WEEKEND

SATURDAY, OCTOBER 24th

ARRIVAL | DINNER | FALL POP-UP EVENT

Arrive in the Chicago area and get settled into the hotel before we kick things off.

That evening, we’ll head out for a tasty dining experience before making our way to one of Chicago's biggest fall pop-up events for a night of fall fun.. pumpkins, attractions, entertainment, games, food, drinks, photo opportunities, and more.

...and we’re not just showing up. We’re going in full costume!

Costumes are actually encouraged at the festival, so bring your creativity and come ready to have some fun. This is our final hike weekend of the year, so we’re starting the celebration on night one.

----------

SUNDAY, OCTOBER 25

STARVED ROCK | MATTHIESSEN | CHICAGO

 

We won’t be starting extremely early, but we’ll get an early start on the trails.

Our first stop will be Starved Rock State Park, where we’ll take on our longer hike, approximately 4 miles through some of the most beautiful fall scenery in the area.

From there, we’ll head to neighboring Matthiessen State Park for our second hike. This trail is rated easy, and approx. less than 2 miles, making it a shorter finish while still delivering the most breathtaking views, colorful foliage, and plenty of scenery to take in.

Once we finish hiking, we’ll head back toward Chicago and the rest of the evening is completely yours.

Buddy up for dinner. Check out an attraction. Find some nightlife. Explore Chicago. Simply head back to the hotel, put your feet up, and recover from an exhilarating day on the trails.

MONDAY, OCTOBER 26

PACK UP | HEAD HOME

Enjoy your final morning, pack up, check out, and we’ll head home.

YOUR HOTEL

This 3-star Chicago-area hotel is located near plenty of restaurants, attractions, entertainment, and nightlife, giving you plenty of options throughout the weekend near the Rosemont (O'Hare) area.

Hotel amenities include:

  • Hot breakfast buffet included
  • Fitness center
  • Airport shuttle available for guests flying in
  • 8.4/10 guest rating
 

Flying in? The free airport shuttle makes getting to the hotel even easier!

TRANSPORTATION

Travel Members: Carpooling will be available on a first-come, first-served basis. Gas is to be evenly shared amongst those riding in the vehicle(s) together.

BOOKING & PAYMENT

After securing your spot, you’ll have two options for completing your remaining trip balance:

Pay in full or choose a 2–3 payment plan.

All payment options and deadlines will be provided during booking.

 

CANCELLATION & TRAVEL INSURANCE

All payments are non-refundable. The $50 deposit (Due by 9/7) and any additional payments made toward the trip cannot be refunded or transferred as they are being applied directly to your reservation.

Travel insurance is strongly encouraged to help protect your trip investment in the event of an unexpected cancellation, interruption, or other covered circumstance.

Please select the travel insurance option at booking if you would like coverage.

Please read all trip details, policies, inclusions, payment terms, and requirements carefully before confirming any payment. By submitting your payment, you acknowledge and agree to the listed trip terms and cancellation policy.

ONE LAST HIKE. ONE BIG FINALE.

Fall foliage. Two incredible parks. Costumes. Huge Fall Pop-Up Festival. Chicago food, nightlife, attractions, and plenty of room to make the weekend your own.

October 24–26, 2026 | Illinois

$50 SAVES YOUR SPOT UNTIL SEPTEMBER 7th. HALF DOWN DEPOSIT OR FULL PAYMENT WILL BE REQUIRED AFTER THAT DATE.

Bookings open until October 12th.

Available Packages

PACKAGE 1 - One King Bed Suites (Sleeps up to 2)
Available until October 12, 2026

$355.00
Deposit: $50.00 per room

Book now (17 left)

This suite features one King bed and is available for up to 2 guests.

Your hotel stay includes:

• Complimentary made-to-order breakfast each morning
• Complimentary evening reception
• Indoor swimming pool
• Fitness center
• On-site restaurant and room service
• Complimentary shuttle service to and from Chicago O’Hare International Airport, if needed
• Business center
• Concierge services
• Non-smoking accommodations
• Convenient access to nearby Rosemont dining, entertainment and shopping

Please Note: On-site self-parking is available for an additional fee of $39 per day and is not included in your Hike & Dine trip package. 

 
 
 

PACKAGE 2 - 2 Queen Bed Suite + Sofabed (Sleeps 4-6)
Available until October 12, 2026

$380.00
Deposit: $50.00 per room

Book now (17 left)

This suite features two Queen beds plus a sofa bed and can accommodate up to 6 guests.

Your hotel stay includes:

• Complimentary made-to-order breakfast each morning
• Complimentary evening reception with drinks and light snacks
• Separate living and sleeping areas
• In-room sofa bed for additional sleeping space
• Indoor swimming pool
• Fitness center
• On-site restaurant and room service
• Complimentary shuttle service to and from Chicago O’Hare International Airport
• Business center and concierge services
• Non-smoking accommodations
• Convenient access to nearby Rosemont dining, shopping, and entertainment

Please Note: On-site parking is available for an additional fee of $39 per night and is not included in your Hike & Dine trip package. 

Room occupancy and bedding selections should reflect the number of travelers included in your booking. All guests must be listed during registration.

 

Extra options

The Extravagant Fall Pop-Up Experience
Available until October 12, 2026

$52.00
Deposit: $52.00

Add the extravagant fall pop-up experience to your Chicago weekend for a festive fall night filled with activities, games, drinks, and seasonal fun.

NOTICE: This is a planned group outing that is being promoted for everyone to bring out their costumes and enjoy a fun-filled evening with the group! We would truly appreciate everyone joining us for this activity!

Your ticket includes:

• General admission entry
• Access to the Corn Maze
• One alcoholic or non-alcoholic drink 
• Three axe throws for guests ages 18+
• Access to explore the pop-up and purchase additional activities, food, drinks, and game tickets

Important Information

Your ticket includes a designated entry window, with arrival permitted up to 30 minutes after the scheduled time. Once admitted, you may stay and enjoy the experience for as long as you'd like.

This is an all-ages outdoor event. Guests must be 21+ to consume alcohol and 18+ to participate in axe throwing. Axe throws included with a ticket cannot be shared between guests.

Additional food, beverages, games, and activities are available for purchase on-site. The venue accepts credit cards and Apple Pay only and does not accept cash.

All ticket purchases are final and nonrefundable. This is a 100% outdoor, non-smoking and non-vaping event.

Carpooling
Available until October 12, 2026

$88.00
Deposit: $10.00

  • 6 spots currently available. (Number may go up)
  • First come, first served
  • Convenient transportation to and from the trip destinations throughout the whole weekend
  • Spots are limited and are only secured once payment is completed
  • Carpool assignments and pickup details will be shared with confirmed participants

Travel Insurance
Available until October 12, 2026

$20.00
Deposit: $20.00

  • Added protection for your trip in case unexpected circumstances require a cancellation.
  • Coverage can help protect your hotel accommodations and eligible trip expenses if the trip is cancelled due to a covered event.
  • Designed to provide added peace of mind for circumstances that may affect your ability to travel.
  • Coverage applies according to the terms, conditions, exclusions, and limits of the selected travel insurance plan.

Additional Non-Member Guest
Available until October 12, 2026

$29.00
Deposit: $29.00

NOTICE: If you do not have an Expedition Pass or an Adventure Collective Membership, you will need to purchase this before confirming your booking.

Bringing someone along? The Non-Member Additional Guest Pass allows a registered Hike & Dine traveler to add an additional guest to their trip without requiring that guest to purchase their own Expedition Pass or Adventure Collective Membership.

This option is available for $29 per additional guest and must be connected to a traveler with a valid Expedition Pass or active Adventure Collective Membership.

The Guest Pass includes:

• Eligibility to participate in the trip alongside the registered member/pass holder
• Access to scheduled group hikes, activities, and experiences included with the guest’s booking
• Trail Support Team assistance during the trip
• Group dining arrangements and reservations when included
• Important trip communications and information needed for participation

Guest Passes are valid for one trip only and do not include Adventure Collective Membership or Expedition Pass benefits.

The primary traveler is responsible for adding their guest(s) during the booking process and providing all required guest information. Guest Passes cannot be purchased or used as a standalone alternative to the required Expedition Pass or Adventure Collective Membership.

PLEASE BE SURE TO LIST YOUR GUEST(S) FIRST & LAST NAME ON YOUR BOOKING FORM

All memberships, passes, and guest eligibility will be verified. False or inaccurate submissions may result in a refund or full cancellation of the booking.

Traveling with us regularly? Guests who plan to join multiple Hike & Dine trips are encouraged to purchase their own Adventure Collective Membership for full travel access and member benefits.

NEW PASS: Expedition Pass (Good for One Trip/Month Only)
Available until October 12, 2026

$49.00
Deposit: $49.00

NOTICE: If you do not have an Expedition Pass or an Adventure Collective Membership, you will need to purchase this before confirming your booking.

The Expedition Pass is your single-trip access to a Hike & Dine travel experience. It’s designed for travelers who want to join us for one adventure without committing to a full-year Adventure Collective Membership.

Your Expedition Pass includes:

• Access to book and participate in one Hike & Dine trip
• Access to your trip’s private Travel Hub and traveler resources
• Detailed itinerary, trip information, and important updates
• Trail Support Team assistance throughout the experience
• Organized group dining and restaurant reservations when included
• Access to scheduled hikes, activities, and experiences included with your registered trip
• Group travel communications and planning support leading up to your adventure

A valid Expedition Pass or Adventure Collective Membership is required to participate in all Hike & Dine trips.

The Expedition Pass applies to one trip only and does not provide the year-round benefits, early access, discounts, or additional perks included with the Adventure Collective Membership.

All passes and memberships will be verified after booking. If a traveler indicates that they already have a valid pass or membership and our records show otherwise, the booking may be fully refunded or cancelled in full. Providing false membership or pass information may result in cancellation of the entire booking.

Already have a valid Expedition Pass for this trip or an active Adventure Collective Membership? You do not need to purchase another pass. Simply select the appropriate existing-member/pass holder options when completing your booking.

Want access to more than one adventure? Consider upgrading to the Adventure Collective Annual Membership for a full year of Hike & Dine travel access and additional member benefits.

NEW MEMBERSHIP: Adventure Collective Annual Membership
Available until October 12, 2026

$149.00
Deposit: $149.00

NOTICE: If you do not have an Expedition Pass or an Adventure Collective Membership, you will need to purchase this before confirming your booking.

Upgrade your Hike & Dine travel experience with a full year of the Adventure Collective membership. This option is for travelers who want access beyond a single trip and plan to stay connected to what we have coming next.

Your membership includes:

• Access to book Hike & Dine group trips for one full year
• Early access to upcoming trips and travel announcements
• Priority access to limited carpool availability
• Access to the private Travel Hub with detailed trip resources and updates
• Members-only experiences and quarterly hikes
• Travel concierge support and organized group dining
• Exclusive member and merchandise discounts
• One complimentary Hike & Dine store item valued up to $40
• Additional Adventure Collective perks released throughout your membership year

A valid Expedition Pass or Adventure Collective Membership is required to participate in all Hike & Dine trips.

All passes and memberships will be verified after booking. If a traveler indicates that they have an active pass or membership and our records show otherwise, the booking may be fully refunded or cancelled in full. Providing false membership or pass information may result in cancellation of the entire booking.

Adventure Collective Memberships are valid for one year from the date of purchase.

Already an Adventure Collective member? You do not need to purchase another membership. Simply select the appropriate existing-member options when completing your trip booking.