Chicago: Airports, Riverfront and City Stays
Published by FlyingWithSources checked
Start with the airport on your ticket and the address of your stay. The riverfront can be a first outing once you have settled in; keep the route, weather and your group’s pace in mind.
Find a place to stay
Chicago River · Owner photoCompare flights when you’re ready.
In pictures
Open a photo for a closer look.
01Before you book
Confirm entry documents with the US consulate responsible for your passport and ask your airline about any assistance, pet or baggage arrangements before choosing a fare. Check the arrival airport on every connection.
For your stay, compare the full price and cancellation terms, then ask about the exact entrance, lift and route from your arrival stop. With a stroller or mobility aid, request details about steps and doorways.
02From the airport to the city
CTA’s Blue Line links O’Hare (ORD) with downtown. From Terminal 5, use the Airport Transit System to Terminal 2 and follow the train signs. The Orange Line links Midway (MDW) with the Loop via an enclosed walkway from the terminal.
Check current service hours, disruptions and elevator alerts before leaving. For a transfer, confirm the terminal pickup point, luggage space, any child seat or access request, and the total price in writing.
03Plan a riverfront outing
The owner photograph shows the Chicago River, the Wabash Avenue bridge and the Wrigley Building. Use it as a starting point for a short city outing rather than adding several stops after a long flight.
Ask your accommodation about a suitable route to the riverfront, including ramps or stairs and the return journey. Check the weather before heading out and keep a sheltered alternative in your plan.
04Everyday details and optional courtesies
Ask whether taxes and service charges are included when comparing prices. Check the bill before choosing a tip.
Leave shared paths and entrances clear when stopping for a photograph. Ask permission before including someone in your picture.
Stay a little longer
Find your place to stay
Choose where to stay, add dates if you have them, and continue to accommodation results through Stay22.
Choose a check-in date, then a duration to set check-out.
Still planning? Leave both dates blank to browse.
Your destination: Chicago
Affiliate link through Stay22. FlyingWith may earn a commission if you book. The booking provider handles prices and payment.
Going somewhere else? Search worldwideReuse them on other accommodation searches and in another language. Only the dates are kept; clear them when your trip changes.
What should the property confirm?
Choose the arrangements you want to check before paying.
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Open the free trip checklist →Official sources
Rules and amounts change. Before you rely on anything marked as an official rule, check the source. These are the official pages we used.
- O’Hare and Midway airport connections · Chicago Transit Authority · checked Publishes airport train routes, terminal connections, operating information and service alerts.
- US consulate: entry documents for your passport and trip.
- Your airline: airport, baggage, pets and assistance arrangements.
- Your accommodation or transfer operator: entrances, vehicle access, pickup and cancellation terms.
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Build my eSIM shopping list →Checks before choosing
Installing an eSIM and starting its validity period can be different events. Follow the chosen plan’s instructions. The checklist is a reminder, not an automatic device check.
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- Compare the countries covered, data allowance, validity start, hotspot rules and any speed limits.
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Getting from the airport
Compare the airport’s official public transport and taxi information with a prebooked transfer. Choose based on the whole journey to your accommodation.
GetTransfer is a transfer marketplace. Availability and suitability depend on the offer; a listed vehicle does not confirm accessible transport or a child seat.
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Take these details to your airport pickup quote
Copy these questions into your request. A marketplace listing alone does not confirm a child seat or accessible vehicle.
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Checks before choosing
- Confirm the exact terminal, meeting point, luggage space and contact method if your flight changes.
- Ask for written confirmation of any child seat, pet or mobility requirement before payment.
- Read the total price, waiting policy, cancellation deadline and refund method for the specific offer.
The provider handles prices, booking terms, payment and support. Review the details there before paying.
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