Best time to visit month-by-month
Best time to visit The Gwen, Michigan Avenue Chicago depends on what you want: for milder weather and fewer crowds, aim for April–May or September–October; for warm waterfront activity and rooftop dining, June–August is best but expect higher temperatures and more tourists. If you prefer winter deals and holiday lights (and don’t mind cold or snow), visit November–March, noting the hotel has no on-site pool or full-service spa and wellness is centered on its 24-hour fitness center.
In this guide
January–February: Cold, quiet, good for lower rates
Chicago’s coldest months bring frigid air and regular snow; averages put January near the low 20s°F. If you’re willing to layer up, hotel traffic and crowds on the Magnificent Mile are lighter than in summer.
At The Gwen expect easy access to indoor attractions (museums, The Shops at North Bridge) and quieter dining reservations for Kostali or Upstairs at The Gwen. Note the property does not have a swimming pool; wellness options are the 24-hour fitness center and arrangeable in-room massages.
- Best for: lower-rate stays, holiday lights lingering into January, museum visits
- Drawbacks: cold weather, potential snow and icy sidewalks
- Hotel note: shorter lines for check-in; restaurants and event spaces remain open
| What to expect | Practical tip |
|---|---|
| Cold temps and snow | Bring insulated coat, boots, and traction-friendly shoes |
| Fewer tourists | Easier restaurant and event bookings (Kostali often requires reservations) |
| No pool or on-site spa | Use the 24-hour fitness center or book in-room treatments |
March–May: Variable spring weather and fewer crowds
Spring is the city’s most variable season; March can still be cool with lake breezes while by May temperatures often reach the 60s°F. April–May are widely cited as one of the best times to visit Chicago because weather improves and crowds are smaller than peak summer.
If you want easier access to Millennium Park and the Riverwalk without full summer crowds, this is a strong window. Weekend Tipsy Tea and rooftop service at Upstairs at The Gwen begin to feel more appealing as temperatures moderate.
- Best for: walking the Magnificent Mile, early outdoor sightseeing, lower-to-moderate rates
- Drawbacks: unpredictable weather—pack layers and a light rain jacket
- Hotel note: terrace and rooftop dining become more enjoyable as the season warms
| Month | Typical feel |
|---|---|
| March | Cool, changeable; still winter-like some days |
| April | Crisp, improving; fewer crowds than summer |
| May | Milder, often pleasant for outdoor activities |
June–August: Warmest weather and rooftop season
Summer brings the warmest and most humid weather, with average highs commonly between the mid-70s and mid-80s°F. These months are best for lakefront activities, boat tours, and rooftop dining at Upstairs at The Gwen, where fire pits and terrace seating are in use.
Summer is also the busiest time on the Magnificent Mile; expect higher room rates and fuller restaurants. Reservations are recommended for Kostali and Upstairs at The Gwen, and anticipate more foot traffic around the hotel and The Shops at North Bridge.
- Best for: lake excursions, rooftop dinners and Tipsy Tea weekends, outdoor festivals
- Drawbacks: heat/humidity, larger crowds, higher rates
- Hotel note: book Early for popular room types (Superior Room, Deluxe Room, Junior Suite) and rooftop seating
| Activity | Summer suitability |
|---|---|
| Rooftop dining at Upstairs at The Gwen | Excellent (long hours Fri–Sat; fire pits and terrace open) |
| Beach time at Oak Street Beach | Good—short walk or transit ride from the hotel |
| Walking tours and architecture cruises | Ideal—many operators run frequent summer schedules |
September–October: Best balance — mild weather and events
Early fall is frequently named the single best time to visit Chicago: September often retains summer warmth with far fewer crowds, and October brings crisp air and fall color. This window combines comfortable outdoor temperatures with plenty of cultural events.
Dinner reservations and rooftop visits are usually easier than in July but still enjoyable early in September. The Gwen’s rooftop and terrace remain a convenient base for evening views while you explore the Magnificent Mile and nearby Riverwalk.
- Best for: day and evening outdoor activities, shopping with manageable crowds
- Drawbacks: evenings can cool quickly—pack a light jacket
- Hotel note: terrace and event spaces remain bookable for weddings and private events in pleasant weather
| Month | Why visit |
|---|---|
| September | Warm days, thinner crowds, festival season |
| October | Cooler days, fall foliage, comfortable city walks |
November–December: Holiday atmosphere and events
Late fall into December brings holiday displays, seasonal menus at hotel restaurants, and more frequent cold days and nights. This period is good if you want to see Chicago’s holiday lights and shop the Magnificent Mile with a festive backdrop.
Expect busier weekends around Thanksgiving and early December for holiday shoppers, and check restaurant hours and event schedules in advance. The Gwen’s indoor dining options (Kostali, Upstairs at The Gwen) provide convenient shelter from cold weather.
- Best for: holiday shopping, museum visits, seasonal dining
- Drawbacks: cold weather and increasing chance of snow
- Hotel note: book ahead for holiday weekend stays and special dining experiences like Tipsy Tea when offered seasonally
| What to plan | Recommendation |
|---|---|
| Holiday shopping on the Magnificent Mile | Plan weekday visits or early mornings to avoid weekend crowds |
| Outdoor walking tours | Bring warm layers; some days may be icy or snowy |
| Hotel dining and events | Reserve in advance for holiday menus or weekend events |
Practical hotel tips by season
Before booking, note The Gwen charges a daily destination/resort fee and offers valet parking; the property does not have a pool or full-service spa, and its wellness is focused on a 24-hour fitness center. Complimentary basic Wi‑Fi is listed as a standard amenity, though some booking channels may apply conditions or fees.
If you plan to bring pets, verify the pet policy and fees; the hotel’s FAQ lists a cleaning fee plus a per-day charge and weight limits. For business or events, The Gwen has extensive meeting and ballroom space but capacities and fees vary by room and season, so confirm with the hotel or BookResorts agents.
- Check-in/check-out: 3:00 PM / 12:00 PM (noon); early/late requests considered when possible
- Dining: Kostali requires reservations; Upstairs at The Gwen accepts reservations and hosts weekly events (e.g., Wine Wednesdays & Live Jazz)
- Rooms: room types include Superior Room, Deluxe Room, Grand Room, Junior Suite, and multiple suite options — book early for terrace rooms in warm months
| Season | Booking tip |
|---|---|
| Winter (Nov–Feb) | Look for lower rates; confirm restaurant hours around holidays |
| Spring & Fall (Apr–May, Sep–Oct) | Ideal balance—book a few weeks ahead for popular weekends |
| Summer (Jun–Aug) | Reserve rooms and rooftop dining well in advance |
