Share an Adventure

Borrow a few of ours

Every card has the practical part first: what, where, how long, and how to get there. Open the memory behind it if you want to know why it matters to us.

Part 1.

Pick your time

  • Forty-five minutes: the building and the park

    • Draft — not yet curated

    Between things? Walk the building with the "look for this" list, then step out to the park it looks over.

    1. Walk the building · Chicago Athletic Association Hotel · 25 min
    2. Millennium Park · Millennium Park · 20 min

    About 45 min in total.

    From Sara + Tyler Tyler's brief 2026-09-04

  • Two to three hours

    • Draft — not yet curated

    The building, the park, and a drink up on the roof.

    1. Walk the building · Chicago Athletic Association Hotel · 45 min
    2. Millennium Park · Millennium Park · 45 min
    3. Cindy's · Chicago Athletic Association Hotel · 1 h

    About 2 h 30 min in total.

    From Sara + Tyler Tyler's brief 2026-09-04

  • Friday afternoon

    • Draft — not yet curated
    • Details to come

    Sara + Tyler are still writing this: your Friday-afternoon picks for guests who arrive early.

    From Sara + Tyler Tyler's brief 2026-09-04

  • Saturday morning

    • Draft — not yet curated
    • Details to come

    Sara + Tyler are still writing this: a calm Saturday morning before the wedding, once the day's times are confirmed.

    From Sara + Tyler Tyler's brief 2026-09-04

  • With kids

    • Draft — not yet curated
    • Details to come

    Short legs, short stops. Sara + Tyler are still writing this: kid policies and the picks you trust.

    1. Shake Shack · Chicago Athletic Association Hotel · 45 min
    2. Millennium Park · Millennium Park · 45 min
    3. Museum of Ice Cream · Museum of Ice CreamDetails to come

    About 2 h 15 min in total.

    From Sara + Tyler Tyler's brief 2026-09-04

  • For the architecture people

    • Draft — not yet curated
    • Details to come

    Start with the building you are standing in. Sara + Tyler are still writing this: the rest of your Chicago architecture picks.

    1. Walk the building · Chicago Athletic Association Hotel · 1 h

    About 1 h in total.

    From Sara + Tyler Tyler's brief 2026-09-04

  • Food and drink

    • Draft — not yet curated
    • Details to come

    The hotel's own places first; hours and menus stay live links on Explore CAA. Sara + Tyler are still writing this: your picks beyond the building.

    1. Fairgrounds · Chicago Athletic Association Hotel · 30 min · Morning
    2. The Ives · Chicago Athletic Association Hotel · 1 h 30 min
    3. Midōsuji · Chicago Athletic Association Hotel · 1 h 30 min
    4. Cindy's · Chicago Athletic Association Hotel · 1 h · Evening

    About 4 h 30 min in total.

    From Sara + Tyler Tyler's brief 2026-09-04

  • Stay inside the CAA

    • Draft — not yet curated

    A whole day without leaving the building.

    1. Fairgrounds · Chicago Athletic Association Hotel · 30 min · Morning
    2. Walk the building · Chicago Athletic Association Hotel · 45 min
    3. Game Room · Chicago Athletic Association Hotel · 1 h
    4. Topgolf Swing Suite · Chicago Athletic Association Hotel · 1 h
    5. Drawing Room · Chicago Athletic Association Hotel · 1 h
    6. Cindy's · Chicago Athletic Association Hotel · 1 h 30 min · Evening

    About 5 h 45 min in total.

    From Sara + Tyler Tyler's brief 2026-09-04

Part 2.

Plan around the time you have

Part 3.

All the places

Stay inside the CAA · 8 places

Food and drink · 1 place

  • Food and drink

    Michael Jordan's Steakhouse

    • Draft — not yet curated
    • Details to come

    Sara + Tyler are still writing this: which location, and what to order.

    Where
    Michael Jordan's Steakhouse, Sara + Tyler are still writing this: which location, and its address

    From Sara + Tyler Tyler's brief 2026-09-04

Outdoors · 2 places

With kids · 1 place

  • With kids

    Museum of Ice Cream

    • Draft — not yet curated
    • Details to come

    Sara + Tyler are still writing this: which location, what to expect, and whether it suits the kids in our group.

    Where
    Museum of Ice Cream, Sara + Tyler are still writing this: which location you visited, and its address

    From Sara + Tyler Tyler's brief 2026-09-04

Day trip · 1 place

Architecture · 1 place

  • Architecture

    Walk the building

    • Draft — not yet curated

    A self-guided walk through the hotel with our "look for this" list: patterned brick, carved limestone, arched windows, custom stained glass, ornate plaster, and mosaic and marble floors.

    Where
    Chicago Athletic Association Hotel, 12 S Michigan Ave, Chicago, IL 60603
    Plan on
    45 min
    From the CAA
    You are already there.
    Cost
    Free

    From Sara + Tyler Tyler's brief 2026-09-04

Hours, menus, and reservation links for the hotel’s own places live on Explore CAA, each with the day we last checked it.