Hotel / parking help needed for moving daughter

Question

Moving my daughter to Chicago the first weekend in August. That’s also Lollapalooza weekend so we are looking to stay outside the city. We will have two cars so we need free parking and want to be near CTE. Her apartment is in Wicker Park. Any suggestions would be greatly appreciated. We are somewhat familiar with the area but in the past we have flown in and used trains. The whole moving and figuring out cars and parking has me overwhelmed! Thanks!

Answer

Moving to Chicago during Lollapalooza weekend can indeed be overwhelming, especially with two cars and needing parking. Staying outside the city is a smart idea since hotel availability and parking in the city will be limited and expensive. Your main priorities are free or easy parking, access to the Kennedy Expressway (CTE) for getting into Wicker Park, and minimizing stress during the move.

Here are some strategies and hotel areas to consider:

Suburban options near the Kennedy Expressway (I-90/94) — Towns like Oak Brook, Oak Park, Skokie, or Niles are convenient for freeway access, offer more hotels with free parking, and are generally quieter than downtown Chicago during Lollapalooza weekend. These suburbs allow you to drive into Wicker Park without dealing with heavy event traffic for parking long-term.
Hotels with free parking: Look for chain hotels in these suburbs that advertise free parking. Examples include Hampton Inn, Holiday Inn Express, and Fairfield Inn in Oak Brook, Skokie, or near O’Hare. Booking early is crucial, as hotels fill quickly due to the festival.
Alternative strategy: Consider a hotel near a CTA Blue Line station (like Oak Park or Forest Park) with free parking, then use the train to Wicker Park. This avoids the downtown Lollapalooza traffic entirely and may simplify the move.

Specific tips for moving weekend:

Plan your arrival and move-in for early morning or late evening to avoid festival-related congestion.
Reserve two parking spots in advance if possible, either at your hotel or using apps that allow parking reservation near the apartment.
Check Wicker Park street parking rules; moving trucks may need temporary permits if parking in front of the building. Some residential buildings have loading zones.
Have one car as a “cargo shuttle” to make multiple trips if needed, and leave the other parked at the hotel or suburban lot to reduce stress.

In summary, your best approach is:

Stay in a suburb with free parking and direct access to the Kennedy Expressway (Oak Brook, Skokie, or Oak Park).
Consider proximity to the CTA Blue Line if you prefer avoiding downtown driving.
Book early and plan to move during off-peak festival times to minimize traffic issues.

This plan balances convenience, parking availability, and stress reduction while still allowing you to help your daughter settle into Wicker Park.