$86 Cheap flight deals from Chicago (CHI) to Hayward (SJC)
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This Weekend's Flight Deals from Chicago to Hayward
This weekend's flight prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
O'Hare Intl.
SFO
San Francisco Intl.
$417 Roundtrip, just found
$417
Roundtrip
just found
MDW
Midway Intl.
OAK
Oakland Intl.
$444 Roundtrip, found 4 days ago
$444
Roundtrip
found 4 days ago
RFD
Greater Rockford
SFO
San Francisco Intl.
$463 Roundtrip, found 2 days ago
$463
Roundtrip
found 2 days ago
MDW
Midway Intl.
SFO
San Francisco Intl.
$474 Roundtrip, found 4 hours ago
$474
Roundtrip
found 4 hours ago
Airfares from $86 One Way, $173 Round Trip from Chicago to Hayward
Prices starting at $173 for return flights and $86 for one-way flights to Hayward were the cheapest prices found within the past 7 days, for the period specified. Prices and availability are subject to change. Additional terms apply.
ORD
Chicago
SJC
San Jose
$173 Roundtrip, found 1 day ago
$173
Roundtrip
found 1 day ago
ORD
Chicago
SFO
San Francisco
$190 Roundtrip, found 3 hours ago
$190
Roundtrip
found 3 hours ago
MDW
Chicago
SFO
San Francisco
$191 Roundtrip, found 3 days ago
$191
Roundtrip
found 3 days ago
ORD
Chicago
SFO
San Francisco
$205 Roundtrip, found 1 day ago
$205
Roundtrip
found 1 day ago
MDW
Chicago
SFO
San Francisco
$237 Roundtrip, just found
$237
Roundtrip
just found
Hayward economy flight packages
Price found within the past 48 hours. Click for updated prices.
3.0-star property
Sonesta Emeryville - San Francisco Bay Bridge
8.6/10 Excellent! (1,375 reviews)
May 2 - May 5
3 night stay
Chicago (CHI) to Oakland (OAK)
United • Roundtrip • Coach
Price was $529, price is now $375 per person
$375
per person
found 1 day ago
Hotel is really nice but food is incredibly bad. Soggy toast, burnt coffee, terrible quesadilla. Huge mistake trying to eat there
Reviewed on Dec 7, 2025
5.0-star property
Farmhouse Inn
9.4/10 Exceptional! (69 reviews)
Apr 20 - Apr 24
4 night stay
Chicago (ORD) to Oakland (OAK)
American Airlines • Coach
Oakland (OAK) to Chicago (ORD)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,502, price is now $1,781 per person
$1,781
per person
found 3 hours ago
2.5-star property
Elm House Inn
9.6/10 Exceptional! (1,505 reviews)
May 4 - May 7
3 night stay
Chicago (CHI) to Oakland (OAK)
Delta • Non-stop • Coach
Oakland (OAK) to Chicago (CHI)
Frontier Airlines • Non-stop • Coach
Price was $604, price is now $436 per person
$436
per person
found 1 day ago
Amazing Bed and Breakfast. The rooms were so nice, extremely comfortable bed, spacious bathrooms. The staff was AMAZING!!
Reviewed on Jul 28, 2025
Hayward first class flight packages
Price found within the past 48 hours. Click for updated prices.
4.0-star property
Fairmont Sonoma Mission Inn & Spa
8.6/10 Excellent! (1,001 reviews)
Apr 20 - Apr 25
5 night stay
Chicago (ORD) to Oakland (OAK)
American Airlines • Non-stop • FirstClass
Oakland (OAK) to Chicago (ORD)
Alaska Airlines • Non-stop • FirstClass
Price was $3,028, price is now $2,521 per person
$2,521
per person
found 4 hours ago
Needs some upgrading to rooms and spa and charging for parking is something new and unpleasant now.
Reviewed on Jan 26, 2026
4.0-star property
MacArthur Place Hotel & Spa
9.4/10 Exceptional! (855 reviews)
Apr 20 - Apr 25
5 night stay
Chicago (ORD) to Oakland (OAK)
American Airlines • Non-stop • FirstClass
Oakland (OAK) to Chicago (ORD)
Alaska Airlines • Non-stop • FirstClass
Price was $4,696, price is now $3,411 per person
$3,411
per person
found 4 hours ago
A wonderful place to celebrate a special occassion. The spa experience was one of the best I have had and the dining and bar excellent! Our room was perfect with all the amentities we needed. Plus, close to great wine tasting and dining options. The staff really made us feel special too!
Reviewed on Nov 11, 2025
4.0-star property
Syrah by Avantstay Hilltop Haven in Sonoma Private Pool + Patio
6/10 (1 review)
Apr 20 - Apr 25
5 night stay
Chicago (ORD) to Oakland (OAK)
American Airlines • Non-stop • FirstClass
Oakland (OAK) to Chicago (ORD)
Alaska Airlines • Non-stop • FirstClass
Price was $5,330, price is now $4,256 per person
$4,256
per person
found 4 hours ago
More About Flying To Hayward from Chicago
Route Information for Flights from Chicago to Hayward
Origin Airport IATA Code | CHI |
|---|---|
Destination Airport IATA Code | SJC |
Distance | |
Direct Flight Airlines | |
Earliest Flight Arrival | |
Latest Flight Arrival |
Chicago to Hayward
If you are looking to get guaranteed low prices for Chicago to Hayward flights then Orbitz is the place to go. We use cutting edge mobile tools to find the best deals on air tickets and to keep you updated on delays and changes.
Get Package Savings by Booking Flights and Hotels at the Same Time
Using the Orbitz Matrix display, you can see how much you will save on flights from Chicago to Hayward if the discount fare is combined with a hotel. You can also look at hotel reviews, photos and maps of the area, so it will be convenient to make your budget travel plans.
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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.
Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $30 service fee charged by Orbitz. Additional airline charges may apply.
Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.