The Plan.
Three days. One mission. Everything dialed in so nobody has to think — just show up.
🛬 Friday · Oct 2
2–4 PM
Arrive & Check In
Flights land, Ubers to hotel. Drop bags, get situated. Group chat goes live.
5:00 PM
Lobby Up
Everyone downstairs. First round's on the trip organizer. Set the tone.
7:00 PM
Steakhouse Dinner
RPM Steak or Bavette's. Reservation for the group — see Dining tab for details.
10:00 PM
Night Out
River North cocktails. Celeste, The Violet Hour, or Arbella. Keep it upscale, keep it moving.
🌆 Saturday · Oct 3
10:00 AM
Late Breakfast
Shake off Friday. Yolk or The Hampton Social. Coffee, eggs, no rush.
12:00 PM
Explore the City
Riverwalk, Magnificent Mile, Architecture Boat Tour, or just post up at a rooftop bar. Dealer's choice.
1:30 PM
Lunch
Deep dish at Lou Malnati's or Italian beef at Portillo's. This is Chicago — eat like it.
4:00 PM
Free Time / Rest Up
Back to hotel, nap, regroup. Big night ahead.
7:30 PM
Saturday Night Dinner
Maple & Ash or Swift & Sons. See Dining tab for the full lineup.
10:30 PM
Saturday Nightlife
Tao Chicago, PRYSM, or the rooftop at London House. This is the big night — game's tomorrow, act accordingly.
🏈 Sunday · Oct 4 · Gameday
9:30 AM
Gameday Breakfast
Fuel up. Keep it light — you're drinking all day. Hotel lobby or quick diner spot.
10:30 AM
Pregame Bar
Kroll's South Loop or Scout Waterhouse. Put the jerseys on. Start the chants.
11:45 AM
Walk to Soldier Field
15-min walk from South Loop. Take Museum Campus Drive. You'll see the columns — that's it.
12:00 PM
Gates Open
Get in, find your seats, grab the first stadium beer. Soak it in.
1:00 PM
KICKOFF — Jets at Bears
Week 4. 1:00 PM ET. FOX. Let's go.
~4:30 PM
Postgame
Win or lose, we celebrate. Walk to South Loop for postgame food and drinks. Recap the game, talk trash.
6:00 PM
Postgame Dinner
Casual — pizza, wings, whatever hits. Or keep it at the postgame bar.
Evening
Flights Home or One Last Round
Red-eyes out, or squeeze one more night. Either way — you did it right.
Group Chat.
Tap to text the crew, send reminders, or reach anyone directly. Everything opens in your phone's Messages app.
⚡ QUICK MESSAGES
📱 TEXT ANYONE DIRECTLY
P
Paul
📱 Number needed
D
Dave
📱 Number needed
💡 Pro tip: The group text opens your phone's native Messages app with all the numbers pre-loaded. Works on iPhone and Android. Everyone with a number above is included — once Paul and Dave send theirs, we'll add them too.
Game Day.
Everything you need to know for Sunday, October 4 at Soldier Field.
1:00 PM ET
Kickoff · Sunday, October 4, 2026 · FOX
Stadium
Soldier Field
Capacity
61,500
Address
1410 Special Olympics Dr
Gates Open
12:00 PM
📍 Getting There
Soldier Field
- Uber/Lyft: Drop off at 18th Street. Surge pricing is real — order early or walk from South Loop (15 min)
- Walk: From the South Loop hotel district, it's a straight shot down Michigan Ave to Museum Campus
- CTA: Green/Orange/Red line to Roosevelt, then walk east (~15 min)
- No parking: Don't rent a car. Chicago gameday parking is a nightmare
🎒 What to Bring
Pack Smart
- Jersey: Obviously. Rep the green.
- Layers: Early October in Chicago can swing 45–65°F. Bring a jacket.
- Clear bag: NFL clear bag policy — 12×6×12 clear plastic or one-gallon Ziploc
- Phone charger: Portable battery. Your phone will die from photos, bets, and group chat
- Cash: Some vendors are cash-only around the stadium
- Sunglasses: 1 PM sun at lakeside is no joke
🍺 Pregame Spots
Before Kickoff
Kroll's South Loop
Classic Bears pregame bar. Packed on gameday. Cheap beers, big TVs, rowdy crowd. You'll be outnumbered in Jets green — embrace it.
Scout Waterhouse + Kitchen
More upscale pregame option. Craft cocktails, solid food. Good if you want to ease into gameday instead of sprinting.
🌡️ Weather Note: Early October in Chicago averages highs around 62°F and lows near 48°F. Lake Michigan wind makes it feel colder. Layer up — you're sitting outside for 3+ hours.
⚠️ Visiting Fan Tip: Soldier Field fans are passionate but generally chill with visiting fans. Talk your talk, don't start anything. Enjoy the banter. If the Jets win — celebrate smart, not loud.
Where to Eat.
Upscale steakhouses for the big dinners. Chicago staples for everything else. Reservations are a must — book early.
⭐ TOP OF THE LIST
Gene & Georgetti
Chicago's oldest steakhouse — since 1941. Tuscan roots, old-school power-dinner energy. Celebrity photos on the walls, white tablecloths, bone-in steaks the size of your head. This is the real Chicago steakhouse experience — no pretense, just 80+ years of doing it right.
🗺️ Directions
Pequod's Pizza
Forget the tourist deep dish spots — this is the one Chicagoans actually eat at. Famous for the caramelized cheese crust that gets crispy and almost burnt around the edges. Pan pizza done at a level that'll ruin every other slice for you. There's usually a wait — put your name in and grab a drink at Whale Tale next door.
🗺️ Directions
🥩 STEAKHOUSE TIER
RPM Steak
Giuliana & Bill Rancic's spot. Dark, moody, premium cuts. The bone-in ribeye and lobster tail are the move. Perfect for the Friday night "we're here" dinner.
🗺️ Directions
Bavette's Bar & Boeuf
Speakeasy vibes, live jazz, incredible steaks. The shrimp de Jonghe is legendary. Dark leather, low light — the kind of place that makes you feel like you're doing something right.
🗺️ Directions
Maple & Ash
Wood-fired everything. The "I Don't Give a F@#%" menu lets the chef decide for the table — trust it. Great for Saturday night when you want to go big.
🗺️ Directions
Swift & Sons
Chicago's meatpacking heritage turned into a world-class steakhouse. Dry-aged cuts, killer cocktail program. In the heart of Fulton Market's restaurant row.
🗺️ Directions
🍕 CHICAGO STAPLES
Lou Malnati's
The deep dish. Buttercrust, sausage, the works. Don't leave Chicago without it. Hit the Wabash or State St location.
Portillo's
Italian beef, dipped, with hot peppers. Chicago hot dog. Chocolate cake shake. This is the city in a restaurant. Non-negotiable.
Yolk
Brunch/breakfast spot. Huge portions, good coffee, eggs every way. Great Saturday morning hangover cure.
📞 Reservation Tip: For the steakhouses, book 3–4 weeks ahead. Party of 6 on a Friday or Saturday night in October? These places fill up. Use OpenTable or Resy — don't wing it.
After Dark.
Upscale cocktail bars, rooftop lounges, and late-night spots. River North and Fulton Market are your playground.
🍸 COCKTAIL BARS
The Violet Hour
No sign on the door — look for the lightbulb. James Beard Award–winning cocktail bar. No standing, no phone calls, craft cocktails only. Worth the Uber to Wicker Park.
Celeste
Restaurant downstairs, late-night lounge upstairs. After dinner, just head up. Great energy on Friday/Saturday nights without the club chaos.
Arbella
Mediterranean-inspired cocktails. Moody lighting, DJ sets on weekends. Intimate but lively — the kind of place where the night picks up speed.
🏙️ ROOFTOPS & LOUNGES
London House Rooftop
Tri-level rooftop with skyline and river views. October might be the last warm-enough weekend to enjoy it. Check weather — worth it if it cooperates.
Raised · Renaissance Hotel
Urban garden rooftop bar. River views, craft cocktails, more relaxed vibe than the club scene. Good for starting the night before escalating.
🎶 LATE NIGHT
Tao Chicago
The big one. Dinner turns into a scene. If you want the high-energy, bottle-service, see-and-be-seen night — this is it. Get a table or don't bother.
The Bassment
Underground dance club. Hip-hop, electronic, live DJs. Where you end up at 1 AM when nobody's ready to call it.
🚕 Rideshare Reminder: Uber/Lyft surge pricing hits hard after midnight in River North on weekends. Budget $30–50 per ride back to the hotel. Or stay walkable.
Where to Stay.
South Loop puts you walking distance to Soldier Field. River North puts you in the action at night. Pick your priority.
🏨 RECOMMENDED
The Hoxton
Boutique hotel in the heart of Fulton Market restaurant row. Rooftop pool and bar, great design, walkable to nightlife. The cool-kid hotel that doesn't try too hard.
🗺️ Directions
Viceroy Chicago
Luxury pick. Rooftop lounge with skyline views. Gold Coast location is a short Uber to everything. The "we're doing this right" option.
🗺️ Directions
Virgin Hotels Chicago
Fun, modern, great common areas and rooftop. Central location. The "let's not overthink it" option that still delivers.
🗺️ Directions
Hilton Chicago
Closest quality hotel to Soldier Field. Walking distance to the stadium. Classic, reliable. If gameday convenience is the priority — this is the one.
🗺️ Directions
💡 Booking Tip: Book 4–5 rooms for 8 guys. Two per room keeps it comfortable. October is busy in Chicago — book by mid-August at the latest. Check if your hotel has a rooftop bar — pregame views of the skyline before dinner hit different.
The Crew.
Eight deep. Chicago doesn't know what's coming.
P
Paul
The crew
📱 Number needed
D
Dave
The crew
📱 Number needed
📋 Crew Rules
How This Works
- Commit by August 15: Need headcounts for reservations, hotel rooms, and tickets
- Venmo/Zelle deposits: Once you're in, send your share to lock it in
- No flaking: If you commit, you're coming. Tickets and reservations are non-refundable.
- Group chat is law: All logistics go through the group chat. Check it.
- Jersey required: You're showing up in green. No exceptions.
Payments Due.
Running tally of all trip expenses. Jonathan covers upfront — Venmo or Zelle your share when you see it here. No surprises, no "I'll get you later."
Total Spent
$0.00
Per Person
$0.00
Total Collected
$0.00
Outstanding
$0.00
📝 EXPENSE LOG
No expenses logged yet. Jonathan will update this as costs are booked.
👥 WHO OWES WHAT
JM
Jonathan
Trip Organizer · Covers upfront
—
ORGANIZER
J
Jorje
Owes: $0.00 · Paid: $0.00
$0
$0 due
MJ
Maurice
Owes: $0.00 · Paid: $0.00
$0
$0 due
P
Paul
Owes: $0.00 · Paid: $0.00
$0
$0 due
D
Dave
Owes: $0.00 · Paid: $0.00
$0
$0 due
S
Sean
Owes: $0.00 · Paid: $0.00
$0
$0 due
A
Alex
Owes: $0.00 · Paid: $0.00
$0
$0 due
N
Nadiff
Owes: $0.00 · Paid: $0.00
$0
$0 due
💸 How to Pay Jonathan
Send Your Share
- Venmo: @jonathan-mcdermott
- Zelle: 201-321-9330
- Cash: In person works too — just make sure Jonathan marks it here
📣 SEND A REMINDER
Nudge the Crew
Tap to send a friendly payment reminder via text.
📊 How this works: Jonathan logs every shared expense (flights, hotel, tickets, dinners) and updates this page. Each person's balance updates so you always know exactly where you stand. No guessing, no awkward conversations. Pay up = green. Owe = red. Simple.
The Damage.
Rough cost breakdown per person assuming 8 guys, split evenly. Final numbers locked once reservations are booked.
| ✈️ Flights (EWR → ORD round trip) | $200–350 |
| 🏨 Hotel (2 nights, split room) | $250–400 |
| 🏈 Game ticket (upper/mid bowl) | $150–300 |
| 🍽️ Dining (Fri + Sat dinners) | $200–350 |
| 🥃 Drinks & Nightlife | $150–300 |
| 🚕 Ubers & Transport | $75–120 |
| 🍕 Casual food (lunch, breakfast, etc.) | $50–100 |
| Estimated Total Per Person | $1,075–1,920 |
~$1,500
Realistic target per person · all-in · 3 days
💸 Payment Plan
How We Split
- Deposit — $500: Due when you commit. Covers ticket + hotel deposit.
- Balance — remaining: Due 2 weeks before the trip (Sept 18)
- Venmo: @jonathan-mcdermott (or Zelle — ask in group chat)
- Dinners: Split at the table or one card + Venmo after
- Drinks: You're on your own, champ
🎟️ Ticket Strategy: Buy together for seats in the same section. Check StubHub, SeatGeek, and Vivid Seats — prices usually dip 2–3 weeks before the game. Upper deck (300-level) is the value play. Lower bowl if we're feeling it.
Jorje's Guide.
Chicago has one of the best LGBTQ+ scenes in the country. Boystown (Northalsted) on Halsted Street is the main gayborhood — the oldest officially recognized gay neighborhood in the U.S. Andersonville is the chill, upscale second act. Here's the best of both for the weekend.
🌈 GAY BARS · BOYSTOWN
Sidetrack
The anchor of Halsted Street and arguably the best gay bar in Chicago. 15,000 square feet, six rooms, rooftop deck, and famous frozen cocktails. Show Tunes on Friday afternoons, Saturday Night Dance Party, and Sunday Funday are all legendary. This is where everyone ends up — locals and visitors alike. $7 cocktails all day, every day.
🗺️ Directions
Roscoe's Tavern
Boystown institution since 1987. Five bar areas, a dance floor, outdoor patio, and drag shows that keep the crowd invested. Known for great drink prices — they run $1 drink nights regularly. Right across from Sidetrack so you can bounce between the two all night.
🗺️ Directions
Hydrate Nightclub
Where Boystown ends up when everywhere else closes. Open until 4 AM Fridays, 5 AM Saturdays. Top-tier DJs, high-energy dance floor. This is the late-night move — don't show up before midnight.
🗺️ Directions
Charlie's Chicago
Western-themed bar and dance club. Country music, line dancing, drag shows, and karaoke early in the night — then around 1 AM on weekends it flips into a go-go boy after-hours dance club. Wild energy shift that you have to see to believe.
🗺️ Directions
Scarlet
Where the young and stylish crowd meets up. Sleek vibe, strong drinks, and a popular Sunday "Liquid Brunch" starting at 2 PM — $12 bottles of champagne, $4 Bloody Marys. Great way to pregame before or after the Jets game.
🗺️ Directions
🍸 GAY BARS · ANDERSONVILLE & BEYOND
Meeting House Tavern
Chill Andersonville gathering place with pool, darts, skee-ball, board games, and rotating frozen drinks. Drag shows and themed nights throughout the week. A neighborhood spot with real personality — less scene, more community.
🗺️ Directions
Big Chicks
An Uptown gem known for its inclusive atmosphere, unique artwork, and "Sunday Funday" events. Art on the walls, eclectic crowd, and a vibe that's more neighborhood hangout than Halsted Street club. Worth the Uber.
🗺️ Directions
Replay Beer & Bourbon
Arcade-themed bar with vintage games, 26 craft beers on tap, and one of the biggest bourbon selections in Chicago. Chill, fun, and nostalgic — play Donkey Kong with a Manhattan in hand. Locations in both Boystown and Andersonville.
🗺️ Directions
🍽️ GAY-FRIENDLY RESTAURANTS
Kit Kat Lounge & Supper Club
Upscale dining meets drag cabaret. Over 200 martini options, contemporary American menu, and tableside performances by the Kit Kat Divas throughout the night. "South Beach meets Hollywood" energy. This is THE dinner-and-a-show experience in Boystown — book a reservation.
🗺️ Directions
Wood
Six-time Michelin Bib Gourmand winner. LGBTQ-owned, wood-fired shareable plates on a rotating seasonal menu. Sunday brunch is excellent. The most "serious food" option on Halsted Street — upscale without being pretentious.
🗺️ Directions
Drew's on Halsted
American bistro with a popular patio right on Halsted. Solid brunch, dinner, and people-watching. Casual enough for a Saturday lunch but elevated enough that you don't feel like you're eating bar food.
🗺️ Directions
Ann Sather
Cozy Swedish brunch institution famous for its cinnamon rolls. A Boystown-adjacent staple for decades — the perfect low-key Saturday or Sunday morning spot before heading out. Owned by former alderman Tom Tunney, an openly gay Chicago icon.
🗺️ Directions
Elixir
Intimate cocktail lounge in the heart of Andersonville. Craft cocktails and sophisticated bar snacks in a moody, inviting space. Great date-night energy or just a classy place to start the evening before heading to the neighborhood bars.
🗺️ Directions
📅 WHAT'S HAPPENING THAT WEEKEND
Weekend Events
Recurring weekly events at the major Boystown venues — these happen every weekend so they'll be on for Oct 2–4.
🎶 Friday · Oct 2
Sidetrack: T.G.I.F. Show Tunes 3–7 PM → Drag Race viewing 7–9 PM → Friday Night Dance Party 9 PM–2 AM
Roscoe's: Friday drag shows + DJ dance night
Hydrate: Opens late, DJ sets until 4 AM
Roscoe's: Friday drag shows + DJ dance night
Hydrate: Opens late, DJ sets until 4 AM
🐾 Saturday · Oct 3
Sidetrack Dog Day: First Saturday of the month — bring (or pet) dogs 1–5 PM on the rooftop 🐶
Sidetrack: Saturday Night Dance Party 9 PM–3 AM
Hydrate: DJ sets until 5 AM
Charlie's: Country dancing → go-go boy takeover after 1 AM
Sidetrack: Saturday Night Dance Party 9 PM–3 AM
Hydrate: DJ sets until 5 AM
Charlie's: Country dancing → go-go boy takeover after 1 AM
☀️ Sunday · Oct 4 (Gameday)
Scarlet: "Liquid Brunch" starts 2 PM — $12 champagne, $4 Bloody Marys
Sidetrack: Sunday Funday — doors open noon, Show Tunes 3–9 PM, After Dark dance party 9 PM–2 AM
The game is at 1 PM — hit Scarlet pregame or Sidetrack postgame
Sidetrack: Sunday Funday — doors open noon, Show Tunes 3–9 PM, After Dark dance party 9 PM–2 AM
The game is at 1 PM — hit Scarlet pregame or Sidetrack postgame
📍 Getting to Boystown: Halsted Street between Belmont and Grace. Take the Red Line to Belmont and walk east. Uber from River North is ~15 min / $15–20. Walk the Legacy Walk on Halsted — rainbow pylons honoring LGBTQ+ heroes. The rainbow crosswalks and murals are everywhere — you'll know when you're there.
🗺️ Jorje's Recommended Route
The Halsted Crawl
Start at one end, work your way down. The whole strip is walkable.
- Start: Dinner at Kit Kat Lounge (drag show + martinis)
- Stop 2: Sidetrack rooftop for frozen cocktails
- Stop 3: Roscoe's for drag show + dancing
- Stop 4: Scarlet for a stylish nightcap
- Closer: Hydrate until the sun comes up
🚕 Late Night Tip: Boystown is about 20 min by Uber from the South Loop / River North hotel zone. After 2 AM, surge pricing kicks in hard. Coordinate rides back — or just stay out until Hydrate closes at 5 AM on Saturday night and beat the surge entirely.