Chicago skyline lit up at night

November 20–22, 2026 · Central Time

Jeremy & Michele’s Chicago Weekend

City lights, Christmas markets & a little holiday magic.

Friday

Beer, Steak & Illini Basketball

Drive, dinner & the Illini game

Saturday

Chicago Lights & Holiday Nights

6:30 a.m. Train to Chicago · ≈ 10:15 Arrive at The St. Regis · 5:00 Lights Festival at Rebar

Sunday

Breakfast with a View & Christmas Market

10:00 a.m. Culture & Cheer tour check-in · 10:15 Culture & Cheer Tour · 4:05 p.m. Train to Champaign

BookedPlannedFlexibleTravel

Friday, November 20

Beer, Steak & Illini Basketball

Overnight: Coronado Airbnb #7, Champaign

  1. 3:30 p.m.

    Planned

    Michele leaves work

    Head home and get ready to leave.

  2. 4:00 p.m.

  3. Late afternoon

    Flexible

    Triptych Brewing

    Savoy, Illinois

    Planned beer stop before dinner. Arrival time is flexible.

    WebsiteDirections

  4. 6:00 p.m.

    Planned

    Dinner at The Ribeye

    Champaign, Illinois

    Planned dinner time — not a confirmed reservation.

    WebsiteDirections

  5. ≈ 7:15 p.m.

    Planned

    Coronado Airbnb #7

    Coronado Drive, Champaign

    Check in and drop bags.

  6. 7:30 p.m.

    Travel

    Walk to State Farm Center

    Only need to arrive a few minutes before tip-off.

    Directions

  7. 8:00 p.m.

  8. ≈ 10:00 p.m.

    Flexible

    Walk back to Coronado

    Relax for the evening — early wake-up Saturday.

Saturday, November 21

Chicago Lights & Holiday Nights

Overnight: The St. Regis Chicago

Hotel · Sat, Nov 21 – Sun, Nov 22

The St. Regis Chicago

401 East Upper Wacker Drive, Chicago, IL 60601

Booked
  • Superior guest room · one king bed · non-smoking
  • Standard check-in 4:00 p.m. (early check-in requested)
  • Late checkout 3:00 p.m. — guaranteed
WebsiteDirections

  1. 5:00 a.m.

    PlannedTrain #58 · Nov 21 · Champaign-Urbana (CHM)

    Wake up & check train status

    Check Amtrak City of New Orleans #58 before leaving. Delays are possible — don't assume one.

    Check Train StatusAmtrak

  2. 5:55 a.m.

    Travel

    Leave Coronado · coffee & breakfast

    Quick stop at Dunkin' or McDonald's on the way to the station. Keep it quick if the train is on time.

    Dunkin' nearbyMcDonald's nearby

  3. 6:30 a.m.

    Booked

    Train to Chicago

    Illinois Terminal, Champaign (CHM)

    Amtrak City of New Orleans #58 · coach seats for Jeremy & Michele.

    • ✦Depart Champaign-Urbana (CHM) 6:30 a.m.
    • ✦Arrive Chicago Union Station (CHI) 9:15 a.m.
    Train StatusStation map

  4. 9:15 a.m.

    Travel

    Arrive Union Station · walk to hotel

    Allow ≈ 45–60 min walk plus station exit time (planning estimate).

    Walk to St. Regis

  5. ≈ 10:15–10:30 a.m.

    Booked

    Arrive at The St. Regis

    401 East Upper Wacker Drive, Chicago, IL 60601

    Request early check-in. If the room isn't ready, leave luggage with the hotel.

    More details
    • • Early room access is requested, not guaranteed.
    • • Superior guest room · one king bed · non-smoking
    • • Standard check-in 4:00 p.m. (early check-in requested)
    • • Late checkout 3:00 p.m. — guaranteed
    WebsiteDirections

  6. 11:30 a.m.

    Planned

    Light lunch at Avli on the Park

    180 N. Field Blvd., Chicago

    Greek lunch — keep it light before the evening buffet. Flexible time, no reservation.

    WebsiteMenuDirections

  7. ≈ 12:30–2:30 p.m.

    Flexible

    Michigan Avenue window shopping

    Magnificent Mile

    Leisurely browsing along the Mag Mile. No fixed stores or bookings — leave room for crowds and a treat.

    Directions

  8. Afternoon

    Flexible

    Choose a treat stop

    Pick one — skip a long line if it eats into hotel downtime.

    Option A

    Ghirardelli Ice Cream & Chocolate

    400 N. Michigan Ave.

    Chocolate, ice cream, or a shared sweet treat.

    WebsiteMapWalk to hotel

    Option B

    Starbucks Reserve Roastery

    646 N. Michigan Ave.

    Coffee and a look around the Roastery.

    WebsiteMapWalk to hotel

  9. ≈ 3:00–4:30 p.m.

    Flexible

    Hotel downtime & getting ready

    Return around 3:00 if convenient. Relax and get ready once the room is available.

    More details
    • • If early check-in wasn't available, the room may not be ready until standard check-in at 4:00 p.m.

  10. ≈ 4:30 p.m.

    Travel

    Walk to Rebar

    St. Regis → Trump International Hotel & Tower. Allow ≈ 20–25 min (estimate). Aim to arrive for 5:00.

    Walking directions

  11. 5:00–8:45 p.m.

    BookedMain event

    Lights Festival at Rebar

    Trump International Hotel & Tower · 401 N. Wabash Ave.

    “A Front-Row Affair | The Magnificent Mile Lights Festival at Rebar” · reserved window table for two.

    • ✦Holiday dinner buffet for both
    • ✦One specialty cocktail each
    • ✦Window-side seating over the festivities
    More details
    • • Event runs 5:00–9:00 p.m.; we plan to leave at 8:45.
    • • Buffet: roasted tenderloin, stuffed chicken, rigatoni, seasonal vegetables, signature salads, festive sweet treats.
    • • Additional beverages available for purchase.
    Event pageRebar websiteDirections

  12. 8:45 p.m.

    Travel

    Leave Rebar for Hubbard Inn

    Settle the bill first. North on Wabash, west on Hubbard — ≈ 10–15 min (estimate, incl. crowds).

    Walking directions

  13. 9:00 p.m.

    Booked

    Christmas Inn at Hubbard Inn

    110 W. Hubbard St.

    Table for two under Jeremy Lamb. Holiday nightcap after the parade — end time flexible.

    More details
    • • Afterward, head back to the St. Regis — walk or ride if tired.
    WebsiteDirectionsWalk to hotel

Sunday, November 22

Breakfast with a View & Christmas Market

  1. 8:30 a.m.

    Planned

    Breakfast at Miru

    At The St. Regis Chicago

    No reservation needed. Allow ≈ 45 minutes.

    WebsiteMenu

  2. ≈ 9:20 a.m.

    Travel

    Walk to Christkindlmarket

    To Daley Plaza, 50 W. Washington St. Allow ≈ 30–40 min (estimate). Goal: 10:00 check-in.

    Walking directions

  3. 10:00 a.m.

    BookedNorth-end VIP entrance

    Culture & Cheer tour check-in

    VIP entrance on the NORTH end of the market. Have tickets ready on the phone.

  4. 10:15–11:00 a.m.

    Booked

    Culture & Cheer Tour

    Christkindlmarket · Daley Plaza

    Two general-admission tickets · 45-minute guided tour.

    • ✦Souvenir mug + beverage voucher each
    More details
    • • Vendor booths are closed during the tour and open for purchases at 11:00 a.m.
    Tour pageDirections

  5. 11:00 a.m.–12:30 p.m.

    Flexible

    Enjoy the market

    Shopping, food, drinks & exploring. Lunch is market food — keep it loose.

    Market website

  6. 12:30 p.m.

  7. Early afternoon

    Flexible

    Relax, pack & get ready

    Guaranteed late checkout is 3:00 p.m. — we can leave earlier.

  8. ≈ 2:30–3:00 p.m.

    Travel

    Hotel → Union Station (undecided)

    Not yet chosen. Target arrival ≈ 3:30–3:35 p.m.

    Planning option A

    Walk

    Leave around 2:30 p.m.; allow ≈ 45–60 min.

    Walking directions

    Planning option B

    Ride

    Leave around 3:00 p.m.; travel time depends on traffic.

    Driving directions

  9. 4:05 p.m.

    Booked

    Train to Champaign

    Chicago Union Station (CHI)

    Amtrak Illini #393 · coach seats for Jeremy & Michele.

    • ✦Depart Chicago (CHI) 4:05 p.m.
    • ✦Arrive Champaign-Urbana (CHM) 6:36 p.m.
    More details
    • • Chicago boarding gate closes five minutes before departure — that's a cutoff, not a recommended arrival time.
    Train StatusStation map

  10. 6:36 p.m.

    Travel

    Arrive in Champaign

    Collect the car and head back to Forsyth. Sunday dinner is open.

Still to decide

Everything else is settled — just these few things.

  • ◇Champaign overnight train-station parking
  • ◇Sunday St. Regis → Union Station: walk or ride
  • ◇Sunday evening dinner, if wanted