5 Days in Chicago for Chicago Marathon

Question

Just looking for some ideas on transit, food, shopping and sightseeing. I. will arrive in Oct 9 with my hubby (he's not running) for my first marathon on Sunday Oct 12. it will also be my first time in Chicago. We are staying at a hotel in the riverwalk area. I'm trying to determine what i can do while trying to rest and not overdo it. I'm deciding between uber or public transit for transport to/from the airport, to/from Expo in McCormick Place and to/from the hockey game (Monday night, i really wanted to go Saturday to see the Canadiens but super early day Sunday). There is a cute marathon themed transit pass, but i cant pre-order it from Canada. The other main thing i need to figure out is food.I will need to pick up some grocery items but will also need some reasonable places for restaurant or takeout meals. I'm not sure where deep dish pizza goes, probably not on the Saturday before the race. Many pasta places are full, so i may need takeaway, or Ubereats etc. I do have reservations for dinner on Sunday with a group from here. i do want yo do some touristy things as I've never been to Chicago and my husband loves shopping for records/vinyl/lps. He has one or more Reckless Records locations pinned, not sure if there are other things..

Thursday - arrive in the evening, eat, maybe get groceries

Friday - Expo and maybe shakeout

Saturday - maybe shakeout run, chill, eat, low energy tourist stuff, light shopping

Sunday - race, celebrate, eat with team mates.

Monday - tourist stuff if i can move, Hockey game, eat Chicago things

Tuesday - leave early

Answer

Chicago in October is an exciting time, especially around the marathon. Since you’re staying near the Riverwalk, you’re centrally located and can make good use of public transit, walking, and selective rideshares. Here’s a detailed guide for your five-day stay balancing race prep, sightseeing, and your husband’s interests.

Transit Options

From O’Hare (ORD) or Midway (MDW) to downtown, you have a few options:

Uber/Lyft: Convenient, especially with luggage, and can be cost-effective for a family of two or small group. Travel times: O’Hare ~35–50 min, Midway ~25–40 min depending on traffic.
Public Transit: CTA Blue Line from O’Hare (~45–50 min to downtown) or Orange Line from Midway (~35–40 min). Fare is $5 from airport to downtown. Efficient if you want to avoid traffic.
For Expo at McCormick Place, CTA Red Line southbound will get you there in about 25–30 minutes from downtown; walking from the station to the expo is short.
Hockey game at United Center (Monday): CTA Green Line westbound to Clinton Station (~20 min from Riverwalk area), short walk to arena.

Since you can’t pre-order the marathon transit pass from Canada, pay-per-ride Ventra cards or single rides work fine; the pass is mostly a convenience for unlimited rides.

Food & Grocery

Since you’ll need groceries for light meals and race prep:

Local grocery options near downtown: Mariano’s, Jewel-Osco, or Whole Foods.
Takeaway/pickup pasta options: Eataly (pasta and carbs to-go), local Italian delis, or use UberEats/Doordash for delivery.
Pre-race and low-energy meals (Friday-Saturday): Simple carbs, salads, grilled chicken, rice bowls — consider Sweetgreen, Protein Bar, or Panera for convenience.
Avoid heavy deep-dish pizza before the race. Post-race, Lou Malnati’s, Giordano’s, or Pequod’s is a classic treat.

Thursday – Arrival Evening

Check into hotel, settle in, and get groceries for pre-race meals/snacks.
Light dinner nearby: casual café or sandwich/pasta spot. Recommendations: Portillo’s for fast casual, or a local café near Riverwalk.

Friday – Expo & Shakeout

Visit the Chicago Marathon Expo at McCormick Place. Allow 2–3 hours for bib pickup, shopping, and checking out vendors.
Optional shakeout run: 2–3 miles along the Lakefront Trail — very scenic, flat, and safe.
Lunch: grab something easy near the expo — sandwiches, salads, or pasta.
Evening: light dinner, early to bed for race prep.

Saturday – Light Tourist & Relaxation Day

Optional morning shakeout: 2–3 miles, Riverwalk or Lakefront Trail.
Low-energy sightseeing: Millennium Park, Cloud Gate, Maggie Daley Park, or the Art Institute (short visit).
Shopping: Husband can visit Reckless Records (two main downtown locations), Vinyl Fetish, or Dusty Groove (for LPs).
Lunch: grab-and-go from cafés or delis; keep carbs high and meals light.
Optional Riverwalk stroll, or relax at hotel. Keep stress low before Sunday.

Sunday – Race Day

Race morning: Eat familiar pre-race breakfast; options nearby include hotel breakfast, Panera, or local café. Avoid trying new foods.
Post-race: Celebrate and eat with teammates (you already have reservations). Hydration and recovery meals are important.
Evening: Rest at hotel; short walk if desired along Riverwalk to stretch legs.

Monday – Sightseeing & Hockey

Morning: If energy allows, explore Navy Pier, Architecture Boat Tour (if your husband enjoys architecture), or 360 Chicago Observation Deck for views.
Lunch: Light meal — sandwiches, salad, or smoothie bowls.
Afternoon: Optional shopping along Magnificent Mile.
Evening: Hockey game at United Center. Dinner either at game or nearby restaurant; Chicago-style hot dogs or casual fare are convenient.

Tuesday – Departure

Early breakfast or grab-and-go items.
Transit to airport: Uber/Lyft for convenience with luggage, or CTA if timing allows.

Tips:

Use public transit for cost-efficiency but Uber/Lyft for airport, expo, or hockey game if tired or with luggage.
For sightseeing before/after race, choose locations that are walkable from your hotel to avoid unnecessary strain.
Plan light, high-carb meals Friday/Saturday, and hydrate consistently. Keep dinners simple and easily digestible.
Lakefront Trail is a runner-friendly path for shakeouts; you can access it from multiple points near downtown.

With this balance of light sightseeing, careful transit planning, and strategic meals, both you and your husband can enjoy your first Chicago Marathon experience while seeing the city without overdoing it.

5 Days in Chicago for Chicago Marathon

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