A close day trip from The Gwen: Navy Pier or lakeside

From The Gwen, Navy Pier is an easy lakeside day trip: it’s roughly a 15–20 minute walk east along Grand or Illinois Street, or a short ride by bus or water taxi. If you prefer a quieter lakeside option, Oak Street Beach and the Lake Michigan shoreline are a 10–20 minute walk north from Michigan Avenue.
In this guide
How to get there from The Gwen
Walking to Navy Pier from The Gwen follows an eastward route (Grand Avenue or Illinois Street) and typically takes about 15–20 minutes on foot according to local guides. If you prefer not to walk, there are convenient public-transit and water-taxi options.
Oak Street Beach and the lakeshore are north along Michigan Avenue; the walk from the hotel to Oak Street Beach is usually about 10–20 minutes depending on your pace and exact route.
- Walk: 15–20 minutes to Navy Pier; 10–20 minutes north to Oak Street Beach.
- Bus: CTA routes that run along Michigan Avenue can shorten travel time to the lakeshore or pier.
- Water taxi: seasonal service runs from locations near the Magnificent Mile and can drop you closer to Navy Pier (check current schedules).
| Option | When to use |
|---|---|
| Walk | Good in fair weather and for a scenic city stroll along Grand or Illinois streets |
| Bus / CTA | Useful if you want to avoid walking or when weather is poor |
| Water taxi | Scenic, seasonal choice that lands near pier attractions; varies by schedule |

What you’ll find at Navy Pier
Navy Pier is a long public pier on Lake Michigan with rides, restaurants, public gardens, performance venues, and skyline views. It’s a family-friendly spot with a mix of indoor and outdoor activities.
Expect casual dining options, concession stands, and seasonal events; details and current attractions change over time, so check Navy Pier’s official schedule before you go.
- Rides and family attractions on the pier
- Restaurants and seasonal pop-ups
- Event and performance spaces (check current listings)
| Attraction type | What to expect |
|---|---|
| Rides & amusements | Family-oriented options and views of the skyline |
| Dining | Casual restaurants and stands along the pier |
| Events | Seasonal concerts, festivals, and public programming |
Lakeside alternatives: Oak Street Beach and the Lakefront
If you want a quieter lakeside experience, Oak Street Beach is a popular city beach near the Magnificent Mile and an easier walk from Michigan Avenue than the pier. It’s a good spot for sun, people-watching, and skyline views.
The Lakefront Trail and nearby stretches of shoreline also allow for biking or walking with uninterrupted lake views—The Gwen provides complimentary bicycles you can use to explore the lakefront and Riverwalk.
- Oak Street Beach: close to the Magnificent Mile, suited to sunbathing and skyline photos
- Lakefront Trail: multiuse path for walking, running, and biking
- Bring layers: lake breezes can be cooler than downtown temperatures
| Spot | Best for |
|---|---|
| Oak Street Beach | Beach time and skyline photography |
| Lakefront Trail | Biking and extended lakeside walks |
| Navy Pier shoreline | Pier attractions with lake views |

How to plan your day (timing & tips)
Morning: head to the lake for a quieter experience—Oak Street Beach and the Lakefront Trail are calmer in the morning hours. Afternoon: Navy Pier is livelier with more food and attraction options.
If you plan to return to The Gwen for dinner or to use hotel facilities, allow extra time for crowds and transit—Upstairs at The Gwen on the rooftop accepts reservations and can be a convenient evening option after a lakeside day.
- Check Navy Pier event calendars for special events that affect crowding and hours.
- Bring sunscreen and water in summer; winters are cold and windy by the lake.
- Reserve tables for dinner—Kostali and Upstairs at The Gwen accept reservations.
| Part of day | Recommended activity |
|---|---|
| Morning | Walk the Lakefront Trail or visit Oak Street Beach |
| Afternoon | Explore Navy Pier attractions and casual dining |
| Evening | Return to The Gwen for rooftop dining at Upstairs at The Gwen |

Practicalities: accessibility, gear, and family notes
The Gwen lists accessible public areas and accessible rooms; the Chicago lakefront, many sidewalks, and Navy Pier also provide accessible routes, though surfaces and crowding can affect navigation—check specific access details before you travel.
There’s no on-site pool at The Gwen, so if your trip centers on swimming, plan alternatives. The hotel does offer luggage storage, complimentary basic Wi‑Fi, and a 24-hour fitness center if you want to return to the property for facilities after your outing.
- The Gwen: luggage storage available and wheelchair-accessible public areas.
- No hotel pool or full-service spa on site—plan lake or community-pool options elsewhere if needed.
- Bring comfortable walking shoes and a light jacket for lake breezes.
| Need | Note |
|---|---|
| Wheelchair access | Hotel has accessible rooms; check accessibility at each lakeside site |
| Children | The Gwen welcomes children of all ages; Navy Pier is family-friendly |
| Swimming | No hotel pool; beach swimming depends on conditions and lifeguard schedules |
Eat and drink near the lake and back at The Gwen
Navy Pier has multiple casual dining options on the pier itself and nearby restaurants a short distance inland. If you prefer a hotel dining experience after your day out, The Gwen offers Upstairs at The Gwen (rooftop American dining and cocktails) and Kostali (Mediterranean on the lobby level).
Tipsy Tea runs on weekends as a themed afternoon tea experience at The Gwen’s Upstairs venue and can be a festive return activity if you’ll be back in the early afternoon. Reservations are recommended for Kostali and helpful for Upstairs at The Gwen.
- Upstairs at The Gwen: rooftop dining, accepts reservations, casual dress code.
- Kostali: Mediterranean dining on the lobby level; Smart Casual dress code and reservations required.
- Tipsy Tea: weekend afternoon tea experience at Upstairs (Sat–Sun), check current schedule.
| Hotel venue | When open / notes |
|---|---|
| Upstairs at The Gwen | Breakfast through late-night service; reservations recommended |
| Kostali | Dinner service; reservation required |
| Tipsy Tea | Weekend afternoon tea experience (check days/hours) |


